☆ 4.5 Review

Mechanochemical synthesis of organohalogen compounds: a synthetic chemist's view

RUSSIAN CHEMICAL REVIEWS (2023)

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Article Chemistry, Applied

Safety Considerations and Proposed Workflow for Laboratory-Scale Chemical Synthesis by Ball Milling

Ian Priestley et al.

Summary: Chemical reactions in a ball mill and without a bulk reaction solvent have different safety profiles compared to stirred solution reactions. We present and describe steps for researchers to consider the hazards and measures to minimize risks to themselves and their colleagues.

ORGANIC PROCESS RESEARCH & DEVELOPMENT (2023)

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Review Chemistry, Multidisciplinary

Advancing mechanochemical synthesis by combining milling with different energy sources

Valentina Martinez et al.

Summary: Mechanochemical processing is an efficient and unique tool for the synthesis and transformation of various materials. Recent advancements combine mechanochemical reactivity with other energy sources, achieving reactions not possible with traditional methods. Thermo-mechanochemistry, sono-mechanochemistry, electro-mechanochemistry, and photo-mechanochemistry represent significant advances in modern mechanochemistry, introducing a new level of solid-state reactivity.

NATURE REVIEWS CHEMISTRY (2023)

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Review Chemistry, Multidisciplinary

The Rise of Trichlorides Enabling an Improved Chlorine Technology

Merlin Kleoff et al.

Summary: Chlorine plays a vital role in the industrial production of global materials. Recent research has shown that polychlorides have immense industrial potential and can be used for chlorine storage and chlorination reactions. The ionic liquid [NEt3Me][Cl-3] offers similar reactivity to chlorine gas but with a better safety profile, making it an ideal candidate for chlorine storage. Furthermore, [NEt3Me][Cl-3] can be directly used as a chlorination reagent for downstream processes, leading to a more practical and safer chlorine industry.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2023)

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Review Chemistry, Multidisciplinary

4′-Fluoro-nucleosides and nucleotides: from nucleocidin to an emerging class of therapeutics

Phillip T. Lowe et al.

Summary: This review discusses the history and development of 4'-fluoro-nucleosides, tracing their origin from the discovery of the rare fluorine-containing natural product nucleocidin. Nucleocidin, which contains a fluorine atom at the 4'-position of its ribose ring, has played an important role in inspiring the exploration of 4'-fluoro-nucleosides as a privileged motif for nucleoside-based therapeutics.

CHEMICAL SOCIETY REVIEWS (2023)

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Review Chemistry, Multidisciplinary

A Review on Mechanochemistry: Approaching Advanced Energy Materials with Greener Force

Xingang Liu et al.

Summary: Solvent-free and environmentally friendly mechanochemistry is a promising alternative to traditional liquid-phase reactions, utilizing mechanical energy to promote chemical transformations and design complex molecules and nanostructured materials, accelerating reaction rates and efficiencies. This review discusses the latest advances in mechanochemistry for energy materials preparation and modification, and proposes next-generation advanced energy materials.

ADVANCED MATERIALS (2022)

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Article Chemistry, Organic

Multi-faceted reactivity of N-fluorobenzenesulfonimide (NFSI) under mechanochemical conditions: fluorination, fluoro- demethylation, sulfonylation, and amidation reactions

Jose G. Hernandez et al.

Summary: In this study, we investigated the reactivity of NFSI by ball milling and found that it can engage in various reactions in mechanochemical processes. Mechanochemical reactions offer advantages such as solvent-free conditions, short reaction times, and comparable or higher yields compared to solvent-based reactions.

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY (2022)

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Review Chemistry, Multidisciplinary

A guide to direct mechanocatalysis

Suhmi Hwang et al.

Summary: The article discusses the concept, historical evolution, and synthesis tool guidance of direct mechanocatalysis. It highlights the impact of milling parameters, catalysts and additives, the scope of reactions, and the hypotheses on the mechanisms of mechanocatalytic transformations.

CHEMICAL COMMUNICATIONS (2022)

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Review Chemistry, Multidisciplinary

Biological Utility of Fluorinated Compounds: from Materials Design to Molecular Imaging, Therapeutics and Environmental Remediation

Cheng Zhang et al.

Summary: This review discusses the applications of fluorinated molecules in bioengineering and nanotechnology, with a focus on controlling fluorine-fluorine interactions and understanding their impact on biological behavior. The controlled introduction of fluorine and its interactions can provide advantages in imaging, therapeutics, and environmental applications.

CHEMICAL REVIEWS (2022)

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Review Chemistry, Multidisciplinary

Mechanochemical Organocatalysis: Do High Enantioselectivities Contradict What We Might Expect?

Matthew T. J. Williams et al.

Summary: Ball mills input energy by pulverising contents of the jar to samples, while enantioselective organocatalytic reactions proceed through perceived transition states. This review focuses on the combination of organocatalytic reactions with mechanochemical ball milling conditions, with particular emphasis on stereoselectivity control.

CHEMSUSCHEM (2022)

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Review Chemistry, Organic

Facile and Environment-friendly Fluorinations using Ionic Liquids

Komal Jakhar

Summary: Recent innovations in fluorination techniques highlight the significant role of ionic liquids in fluorotransformations, such as the use of tagged ionic liquids in nucleophilic fluorinations, ionic liquid assisted biological fluorination, enantioselective fluorinations using chiral electrophilic reagents in ionic liquid media, task-specific ionic liquids in electrochemical fluorinations with mediators, and ionic liquid promoted synthesis of medicinally important fluorinated heteroaromatics and radiopharmaceuticals.

CURRENT ORGANIC SYNTHESIS (2022)

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Review Chemistry, Organic

Manufacturing Approaches of New Halogenated Agrochemicals

Peter Jeschke

Summary: To ensure sustainability, the agrochemical industry faces challenges in providing high-quality food, water use, environmental impact, and growing world population. Developing new agrochemicals with improved efficacy and favorable environmental profiles is essential, with the introduction of halogen atoms as an important tool to influence physico-chemical properties.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2022)

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Review Chemistry, Organic

Sustainable Mechanosynthesis of Biologically Active Molecules

Ophelie Bento et al.

Summary: This Review focuses on the applications of synthetic mechanochemistry in the preparation of known APIs and evaluated bioactive molecules. Three families of compounds, including heterocyclic compounds, metal complexes, and peptides, are discussed. The advantages of mechanochemistry approach are highlighted in terms of green chemistry and efficacy.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2022)

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Review Chemistry, Multidisciplinary

A Perspective on Late-Stage Aromatic C-H Bond Functionalization

Li Zhang et al.

Summary: Aromatic C-H late-stage functionalization poses challenges in terms of reactivity, selectivity, and substrate scope, but also shows potential for development. It is necessary to address current challenges and explore new strategies and directions for growth.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2022)

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Article Biochemistry & Molecular Biology

Mechanochemical Applications of Reactive Extrusion from Organic Synthesis to Catalytic and Active Materials

Emanuela Calcio Gaudino et al.

Summary: In the past, mechanochemical methods in organic synthesis were considered as curiosities, but in the last two decades, perceptions have shifted and this technology is now recognized as a greener and more efficient method. The availability of diverse ball mills has contributed to its development. However, the batch nature of mechanochemical methods has limited their industrial scale-up. Reactive extrusion, a new technique that activates chemical reactions with mechanical forces in a continuous flow, offers a promising solution. This environmentally friendly method allows for miniaturization of production plants, removing organic solvents and operating in a flow mode, while also offering simplicity, safety, and cleanliness.

MOLECULES (2022)

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Review Chemistry, Multidisciplinary

Halide-containing organic persistent luminescent materials for environmental sensing applications

Feiyang Li et al.

Summary: Recent years have seen significant progress in the development of organic persistent luminescent (OPL) materials, with a particular focus on their applications in environmental sensing. The review summarizes the current status of halide-containing OPL materials for environmental sensing, discussing photophysical processes, luminescence mechanisms, and applications such as sensing temperature, oxygen, H2O, UV light, and organic solvents. Challenges and future research opportunities in the field are also addressed, aiming to provide guidance for material design of OPL sensors and exploring new directions for organic optoelectronics applications.

CHEMICAL SCIENCE (2022)

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Article Chemistry, Organic

Mechanochemical Aliphatic Iodination (and Bromination) by Cascaded Cyclization

Ankita Bal et al.

Summary: In this study, oxazoline derivatives were successfully synthesized from N-allyl benzamides through a mechanochemical cascaded cyclization and halogenation using N-iodo- and N-bromosuccinimides as bifunctional reagents.

ASIAN JOURNAL OF ORGANIC CHEMISTRY (2022)

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Article Chemistry, Applied

Mechanochemical Direct Fluorination of Unactivated C(sp3)-H Bonds

Sehye Min et al.

Summary: The mechanochemical fluorination of unactivated C(sp(3))-H bonds has been achieved using N-fluorobenzenesulfonimide as both a precursor of the hydrogen-atom-transfer reagent and a bench-stable fluorine source. Control experiments have confirmed the essential role of mechanical energy in this reaction.

ADVANCED SYNTHESIS & CATALYSIS (2022)

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Article Chemistry, Organic

Electrophilic fluorination of heterocyclic compounds with NF reagents in unconventional media

Gennady I. Borodkin et al.

Summary: This study summarizes and analyzes the data on the electrophilic fluorination of heterocyclic compounds with NF reagents in unconventional media (ionic liquids, water and aqueous solutions, solvent-free media). The effect of the medium and the problem of selectivity were particularly considered.

CHEMISTRY OF HETEROCYCLIC COMPOUNDS (2022)

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Article Chemistry, Multidisciplinary

anti-Markovnikov Iodofluorination of Alkenes

Bai-Yu Qian et al.

Summary: In this paper, a convenient anti-Markovnikov iodofluorination of alkenes was described using Selectfluor/(Bu4NI)-Bu-n as the reagent. The reaction showed a broad substrate scope, good functional group tolerance, and the ability to construct various C-F bonds.

CHEMISTRY-AN ASIAN JOURNAL (2022)

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Review Biochemical Research Methods

Synthetic metabolism for biohalogenation

Antonin Cros et al.

Summary: We suggest that deploying synthetic metabolism tailored for biohalogenation presents a unique opportunity for economically attractive and environmentally friendly organohalide production.

CURRENT OPINION IN BIOTECHNOLOGY (2022)

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Review Biochemistry & Molecular Biology

New Halogen-Containing Drugs Approved by FDA in 2021: An Overview on Their Syntheses and Pharmaceutical Use

Davide Benedetto Tiz et al.

Summary: This review discusses the FDA-approved drugs in 2021 that contain at least one halogen atom. The synthesis and therapeutic uses of these drugs are presented, highlighting the growing importance of halogens, particularly fluorine and chlorine, in the development of drugs for various diseases.

MOLECULES (2022)

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Article Chemistry, Inorganic & Nuclear

Mechanistic Study of the Mechanochemical PdII-Catalyzed Bromination of Aromatic C-H Bonds by Experimental and Computational Methods

Dajana Baris et al.

Summary: The mechanism of mechanochemical Pd-II-catalyzed selective bromination of the carbon-hydrogen bond in azobenzene was investigated using in situ time-resolved Raman spectroscopy and quantum-chemical calculations. It was found that the reaction pathway via monomeric palladacycle is more efficient, offering better yields and faster reactions.

ORGANOMETALLICS (2022)

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Article Chemistry, Physical

Synthesis and Selected Transformations of 2-Unsubstituted Imidazole N-Oxides Using a Ball-Milling Mechanochemical Approach

Grzegorz Mloston et al.

Summary: Synthetically relevant 2-unsubstituted imidazole N-oxides were successfully synthesized using the ball-milling mechanochemical method. This approach not only expanded the scope of the known method, but also enabled the preparation of previously little known N(1)-aryl-substituted derivatives. These derivatives are important starting materials for the synthesis of more complex imidazole-based organic materials. Additionally, the study also investigated selected one-pot mechanochemical transformations including N- and O-alkylations as well as sulfur transfer reactions.

CATALYSTS (2022)

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Review Chemistry, Multidisciplinary

A Fruitful Decade of Organofluorine Chemistry: New Reagents and Reactions

Feng-Ling Qing et al.

Summary: The development of synthetic methods for introducing fluorine atoms and fluoroalkyl groups into organic molecules has received increased attention. Synthetic organic chemists have made significant contributions in the field of organofluorine chemistry and the newly developed methods are typically safer and more effective than traditional methods.

CCS CHEMISTRY (2022)

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Article Biochemistry & Molecular Biology

Mechanochemical Approach towards Multi-Functionalized 1,2,3-Triazoles and Anti-Seizure Drug Rufinamide Analogs Using Copper Beads

Dhananjay Bhattacherjee et al.

Summary: Highly regiospecific azide-alkyne cycloaddition (AAC) reactions have been achieved under mechanochemical conditions. Cu beads were used for efficient synthesis of complex compounds without generating unwanted byproducts. High-speed ball milling strategy was applied for the synthesis of pharmaceutical agents and structural confirmation.

MOLECULES (2022)

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Review Chemistry, Applied

Mechanochemically Induced Cross Dehydrogenative Coupling Reactions under Ball Milling

Ilya N. Egorov et al.

Summary: This review highlights the various applications of cross dehydrogenative coupling reactions under ball milling for the synthesis of useful molecules in a more efficient and convenient manner.

ADVANCED SYNTHESIS & CATALYSIS (2022)

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Article Chemistry, Organic

Mechanochemical halogenation of unsymmetrically substituted azobenzenes

Dajana Barisic et al.

Summary: This study describes the direct and selective mechanochemical halogenation of C-H bonds in unsymmetrically substituted azobenzenes using N-halosuccinimides as the halogen source in a ball mill. The reaction occurs in the absence or presence of PdII catalysts depending on the azobenzene substrate used. In situ Raman spectroscopy, ex situ NMR spectroscopy, and PXRD analysis were used to gain insight into the reaction dynamics and characterization of the products. The different 4,4'-substituents of azobenzene were found to have a strong influence on the halogenation time and mechanism.

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY (2022)

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Article Chemistry, Organic

Automated grindstone chemistry: a simple and facile way for PEG-assisted stoichiometry-controlled halogenation of phenols and anilines using N-halosuccinimides

Dharmendra Das et al.

Summary: A green and facile mechanochemical method for the catalyst-free halogenation of phenols and anilines was developed using a simple electrical mortar and PEG-400 as the grinding auxiliary. The reaction proceeded in good yields within a short reaction time, and the selectivity was controlled by the stoichiometry of N-halosuccinimides (NXS). PEG-400 played a key role in controlling the reactivity and improving regioselectivity.

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY (2022)

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Article Chemistry, Multidisciplinary

Mechanochemical Metal-Free Synthesis of 3-Arylindenones via Unprecedented Aryl Swapping

Liang Li et al.

Summary: This study reveals a novel annulation reaction of benzoic acids with arylalkynes induced by triflic anhydride under an air atmosphere and ball-milling conditions. The reaction proceeds through an unprecedented aryl swapping pathway, resulting in diverse 3-arylindenones. The mechanochemical protocol offers advantages such as no requirement of transition-metal catalysts, ambient conditions, and excellent regioselectivity for the rearrangement products, allowing efficient access to 3-arylindenones containing various functional groups.

CHINESE JOURNAL OF CHEMISTRY (2022)

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Article Biochemistry & Molecular Biology

Mechanochemical Synthesis of Fluorinated Imines

Karolina Ciesielska et al.

Summary: A solvent-free mechanochemical method was used to synthesize a number of imines, including 12 new compounds. The method resulted in short reaction times, high yields, and has potential for large-scale synthesis. It also contributes to environmental protection. The method is versatile and can be applied to the synthesis of chiral benzylamines and similar amines.

MOLECULES (2022)

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Article Chemistry, Organic

Sulfonimidamides by Sequential Mechanochemical Chlorinations and Aminations of Sulfinamides

Steven Terhorst et al.

Summary: The first mechanochemical synthesis of sulfonimidamides is reported in this study. This one-pot, two-step method does not require a solvent or inert conditions. Sulfinamides are rapidly converted to sulfonimidoyl chlorides through oxidative chlorination with N-chlorosuccinimide (NCS) in a mixer mill, followed by substitution with amines to provide a wide range of diversely substituted sulfonimidamides.

ORGANIC LETTERS (2022)

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Review Polymer Science

Evolutions of precision radical polymerizations from metal-catalyzed radical addition: living polymerization, step-growth polymerization, and monomer sequence control

Masami Kamigaito

Summary: Metal-catalyzed Kharasch addition or atom transfer radical addition (ATRA) is a highly efficient radical reaction for controlled syntheses of organic molecules. This review focuses on the development of metal-catalyzed living radical polymerizations, which offer control over various aspects of vinyl polymer structures. The article discusses reversible activation of carbon-halogen bonds, step-growth radical polymerizations of designed monomers, simultaneous chain- and step-growth radical polymerization for degradable vinyl copolymers, and vinyl monomer sequence control using iterative ATRAs and other controlled polymerizations.

POLYMER JOURNAL (2022)

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Article Chemistry, Organic

N2,N6-Bis(6-iodo-2-methyl-4-oxoquinazolin-3(4H)-yl)pyridine-2,6-dicarboxamide

Maja Molnar et al.

Summary: A green chemistry method was utilized to synthesize a new compound using mechanochemical synthesis and a choline chloride-based deep eutectic solvent as a catalyst.

MOLBANK (2022)

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Article Chemistry, Organic

From amines to (form)amides: a simple and successful mechanochemical approach

Federico Casti et al.

Summary: Two easily accessible methods for preparing a variety of formylated and acetylated amines under mechanochemical conditions are presented. These two methodologies have complementary features, as they allow for the derivatization of aliphatic and aromatic amines.

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY (2022)

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Review Biochemistry & Molecular Biology

Ionic Liquids as Organocatalysts for Nucleophilic Fluorination: Concepts and Perspectives

Young-Ho Oh et al.

Summary: Ionic liquids (ILs) have great potential as organocatalysts/promoters in chemical reactions, using their ionic nature and interactions with functional groups in substrates to enhance reaction rates. However, the full application of ILs as organocatalysts/promoters has not been achieved yet.

MOLECULES (2022)

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Review Endocrinology & Metabolism

T3 levels and thyroid hormone signaling

Federico Salas-Lucia et al.

Summary: The study indicates that serum T3 levels can accurately predict tissue T3 content and T3 signaling in most tissues, which is of great importance for managing patients with hypothyroidism.

FRONTIERS IN ENDOCRINOLOGY (2022)

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Article Chemistry, Multidisciplinary

Mechanochemical Bromination of Naphthalene Catalyzed by Zeolites: From Small Scale to Continuous Synthesis

Karen J. Ardila-Fierro et al.

Summary: We developed a mechanochemical bromination method catalyzed by zeolites in a ball mill and twin-screw extrusion, enabling continuous reactions of organic substrates. The use of DBDMH as a brominating agent improved the atom economy of the reaction.

CHEMISTRYMETHODS (2022)

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Review Chemistry, Organic

Oxidative Halogenation of Arenes, Olefins and Alkynes Mediated by Iodine(III) Reagents

Luis A. Segura-Quezada et al.

Summary: Iodine(III)-based reagents are widely used in oxidative reactions for structural functionalization, including fluorination, chlorination, bromination, and iodination protocols. These reagents are applied in oxidative halogenation procedures of arenes, olefins, and alkynes, highlighting the discovery and application of new iodine(III)-based halogenating species.

MINI-REVIEWS IN ORGANIC CHEMISTRY (2021)

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Article Chemistry, Analytical

Molecular Basis for the Remarkably Different Gas-Phase Behavior of Deprotonated Thyroid Hormones Triiodothyronine (T3) and Reverse Triiodothyronine (rT3): A Clue for Their Discrimination?

Davide Corinti et al.

Summary: Thyroid hormones play crucial roles in growth, metabolic regulation, and LC-MS has been used to quantify their blood levels. The gas-phase behavior of isomeric thyroid hormones T3 and rT3 was studied, revealing different deprotonation sites and ion-mobility behavior, with rT3 found to be more acidic than T3.

ANALYTICAL CHEMISTRY (2021)

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Article Chemistry, Applied

1,2-Benzothiazine Derivatives from Sulfonimidamides by Metal-Catalyzed Annulation Reactions in Solution and under Solvent-Free Mechanochemical Conditions

Jan-Hendrik Schobel et al.

Summary: Two different protocols were presented for the preparation of three-dimensional aza-analogues of 1,2-benzothiazine 1,1-dioxides from sulfonimidamides. The first method involves a rhodium-catalyzed annulation reaction to produce 4-unsubstituted benzothiazine derivatives, while the second method utilizes an iridium catalyst under solvent-free mechanochemical conditions to obtain products with 3,4-disubstituted thiazine rings.

ADVANCED SYNTHESIS & CATALYSIS (2021)

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Review Chemistry, Applied

Liquid-Assisted Grinding Mechanochemistry in the Synthesis of Pharmaceuticals

Ping Ying et al.

Summary: Liquid-assisted grinding (LAG) has emerged as an innovative solvent-free mechanochemical method with wide applications in the synthesis of various compounds, especially showing superiority in the synthesis of active pharmaceutical ingredients and drug-like fragments.

ADVANCED SYNTHESIS & CATALYSIS (2021)

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Review Chemistry, Multidisciplinary

Decarboxylative Halogenation of Organic Compounds

Andrii Varenikov et al.

Summary: Decarboxylative halogenation is a crucial method for synthesizing organic halides by converting carboxylic acids to the corresponding organic halides. This method involves the synthesis of organic iodides, bromides, chlorides, and fluorides, providing a wide range of methods and advantages.

CHEMICAL REVIEWS (2021)

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Review Chemistry, Multidisciplinary

Fluorinated Pyrazoles: From Synthesis to Applications

Pavel K. Mykhailiuk

Summary: Fluorinated pyrazoles are increasingly important in various fields, with a focus on novel synthetic approaches, reaction mechanisms, and unexplored classes of these compounds.

CHEMICAL REVIEWS (2021)

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Review Chemistry, Inorganic & Nuclear

Advances in fluorescent and colorimetric sensors for anionic species

Daniel A. McNaughton et al.

Summary: This review presents recent developments in fluorescent and colorimetric anion sensors, utilizing various non-covalent interactions and advancements in anion-selective chemodosimeters.

COORDINATION CHEMISTRY REVIEWS (2021)

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Article Chemistry, Physical

Theoretical Study of the Grinding and Homogenization of a Binary Mixture of Reactive Powders in a Mechanical Activator

O. V. Lapshin et al.

Summary: A theoretical study was conducted on solid-phase mechanochemical synthesis in a binary powder mixture during mechanical processing in a mechanoactivator using a mathematical model in a macroscopic approximation. Analytical relationships were obtained for determining the process parameters, providing a method for finding an effective kinetic constant characterizing the degree of homogenization of the powder mixture.

RUSSIAN JOURNAL OF PHYSICAL CHEMISTRY A (2021)

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Review Chemistry, Multidisciplinary

The many flavours of mechanochemistry and its plausible conceptual underpinnings

Robert T. O'Neill et al.

Summary: Mechanochemistry involves diverse phenomena where mechanical load influences chemical reactions, such as motor protein function, organic synthesis in a ball mill, reactions at a propagating crack, chemical actuation, and polymer fragmentation. The rate of deformation in mechanochemistry affects which and how many bonds break, either powering macroscopic motion in otherwise endergonic reactions or being driven by spontaneous chemical reactions. The complexity of mechanochemistry lies in the dynamic coupling between inertial motion at the microscale and changes in chemical bonding across multiple length scales and timescales.

NATURE REVIEWS CHEMISTRY (2021)

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Article Chemistry, Multidisciplinary

Understanding Ball Milling Mechanochemical Processes with DFT Calculations and Microkinetic Modeling

Bruna S. Pladevall et al.

Summary: Mechanochemistry is a new field with potential applications in sustainable chemistry, but its underlying mechanistic foundations are not fully understood. This study used computational tools to analyze mechanically activated procedures, successfully reproducing experimentally reported reaction times. The findings suggest that reactions accelerated by ball milling follow the same mechanism as equivalent reactions in solution.

CHEMSUSCHEM (2021)

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Review Chemistry, Multidisciplinary

Sustainability Assessment of Mechanochemistry by Using the Twelve Principles of Green Chemistry

Karen J. Ardila-Fierro et al.

Summary: Mechanochemistry has become a widely accepted alternative for chemical synthesis due to its efficiency, practicality, and sustainability, satisfying multiple Principles of Green Chemistry.

CHEMSUSCHEM (2021)

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Review Chemistry, Inorganic & Nuclear

Role of Mixing and Milling in Mechanochemical Synthesis (Review)

O. V. Lapshin et al.

Summary: The discussion includes various topics on inorganic mechanochemical synthesis, covering synthesis methods, monitoring techniques, yield control, kinetics, as well as comparisons between thermal and mechanochemical syntheses with a focus on mixing and milling processes. The effects of mechanical treatment on individual particles and mixtures, and the role of macrokinetics in mixing processes, are also examined. Additionally, the basic assumptions for a mathematical model describing the macrokinetics of mechanochemical synthesis in solid + reactive gas and solid + solid systems are outlined.

RUSSIAN JOURNAL OF INORGANIC CHEMISTRY (2021)

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Article Chemistry, Applied

Mechanochemical Transformation of CF3 Group: Synthesis of Amides and Schiff Bases

Satenik Mkrtchyan et al.

Summary: In this study, two mild, solvent-free mechanochemical coupling transformations of CF3 group with nitro compounds were successfully demonstrated, leading to amides or Schiff bases. Ytterbia was used as a catalyst to facilitate the process, which involves C-F bond activation and the use of Si-based reductants/oxygen scavengers. This work represents the first example of utilizing mechanical energy to promote the transformation of the inert CF3 group into other functionalities.

ADVANCED SYNTHESIS & CATALYSIS (2021)

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Review Chemistry, Organic

Development of N-F fluorinating agents and their fluorinations: Historical perspective

Teruo Umemoto et al.

Summary: This review covers the historical development of all N-F fluorinating agents developed to date, including various types of N-F compounds and their derivatives. It discusses the unique properties of fluorine that make fluorinated organic compounds attractive in research, and the usefulness of N-F agents due to their easy handling. The review also chronicles the synthesis, reactions, and relative fluorination power of each reagent from a historical perspective.

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY (2021)

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Article Chemistry, Organic

Mechanochemical-Cascaded C-N Cross-Coupling and Halogenation Using N-Bromo- and N-Chlorosuccinimide as Bifunctional Reagents

Shyamal Kanti Bera et al.

Summary: The study demonstrated the successful synthesis of phenanthridinone derivatives using NBS and NCS as bifunctional reagents under mechanochemical conditions. This approach allowed for the cascaded C-N bond formation and subsequent halogenation reactions, showcasing a potential application of alternative energy sources in chemical transformations.

JOURNAL OF ORGANIC CHEMISTRY (2021)

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Article Biochemistry & Molecular Biology

Ionic Liquid-Assisted Grinding: An Electrophilic Fluorination Benchmark

Pavel A. A. Zaikin et al.

Summary: The influence of liquid additives on the rate and selectivity of mechanochemical fluorination has been demonstrated, with ionic liquids shown to catalyze the reaction and improve the isolation of fluorinated products. A careful choice of additive results in high yields of fluorinated products and low E-factor for the overall process.

MOLECULES (2021)

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Article Chemistry, Multidisciplinary

Mechanochemical N-Chlorination Reaction of Hydantoin: In Situ Real-Time Kinetic Study by Powder X-ray Diffraction and Raman Spectroscopy

Ines C. B. Martins et al.

Summary: In this study, the kinetic profile of the chlorination reaction of N-3-ethyl-5,5-dimethylhydantoin (EDMH) activated and driven by ball milling was investigated. The results show that the reaction progress to equilibrium is similar at different ball sizes, but the induction period and reaction rate are affected by ball size. The research demonstrates a significant correlation between the rate of chemical transformations during the reaction and the volume of the milling balls used.

ACS SUSTAINABLE CHEMISTRY & ENGINEERING (2021)

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Review Chemistry, Organic

Electrophilic and Oxidative Fluorination of Heterocyclic Compounds: Contribution to Green Chemistry

G. I. Borodkin et al.

Summary: The literature data on electrophilic and oxidative fluorination of heterocyclic compounds have been analyzed in terms of green chemistry principles, with a focus on reaction mechanisms and selectivity issues.

RUSSIAN JOURNAL OF ORGANIC CHEMISTRY (2021)

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Review Chemistry, Organic

Halogen bond-induced electrophilic aromatic halogenations

Wanutcha Lorpaiboon et al.

Summary: In recent years, there has been increased interest in utilizing halogen bonds in organic synthesis, particularly in aromatic halogenation reactions. N-Halosuccinimides and 1,3-dihalo-5,5-dimethylhydantoins are commonly used sources of halonium ions due to their easy handling and low toxicity. Recent research has shown that activation of N-haloimides by nucleophilic Lewis base catalysts can lead to a shift in the paradigm of aromatic halogenation.

ORGANIC & BIOMOLECULAR CHEMISTRY (2021)

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Review Chemistry, Multidisciplinary

Halogen bonding in polymer science: towards new smart materials

Robin Kampes et al.

Summary: The halogen bond, while underrepresented in polymer science, shows great potential for designing polymeric materials. Applications of halogen bonding in self-assembly, photo-responsive materials, and self-healing materials are currently expanding.

CHEMICAL SCIENCE (2021)

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Article Chemistry, Multidisciplinary

Accessing novel fluorinated heterocycles with the hypervalent fluoroiodane reagent by solution and mechanochemical synthesis

William Riley et al.

Summary: A new and efficient strategy has been developed for the rapid formation of novel fluorinated tetrahydropyridazines and dihydrooxazines by fluorocyclisation of beta,gamma-unsaturated hydrazones and oximes with the fluoroiodane reagent. Mechanochemical synthesis showed similar yields for fluorinated tetrahydropyridazines compared to conventional solution synthesis, while fluorinated dihydrooxazines were prepared in much better yields through ball-milling.

CHEMICAL COMMUNICATIONS (2021)

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Review Chemistry, Multidisciplinary

Medicinal chemistry strategies for discovering antivirals effective against drug-resistant viruses

Yue Ma et al.

Summary: This article discusses strategies for discovering antiviral compounds specifically designed to combat drug resistance, including targeting proteins, drug conformation, new binding sites, and host factors as potential therapeutic approaches.

CHEMICAL SOCIETY REVIEWS (2021)

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Article Chemistry, Multidisciplinary

Solvent and catalyst-free bromofunctionalization of olefins using a mechanochemical approach

Jonathan Wong et al.

Summary: Bromofunctionalization of olefins is an important chemical transformation, typically utilizing N-bromoimide reagents and catalysts. However, this study demonstrates a solvent and catalyst-free approach to achieving bromofunctionalization of olefins using mechanical force.

RSC ADVANCES (2021)

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Article Chemistry, Multidisciplinary

Synthesis, characterization and antioxidant activity studies of new coumarin tethered 1,3,4-oxadiazole analogues

Vagish Channa Basappa et al.

Summary: In this study, a series of novel substituted 3-(5-phenyl-1,3,4-oxadiazol-2-yl)-2H-chromen-2-one compounds were synthesized using substituted aldehydes and hydrazine hydrates analogues in the presence of Iodine by grinding technique. The structures of the compounds were characterized using spectroscopic techniques. Results showed that compounds 7d and 7i exhibited strong radical scavenging activity, indicating potential antioxidant properties.

JOURNAL OF CHEMICAL SCIENCES (2021)

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Article Chemistry, Multidisciplinary

Mechanochemistry of fluoride solids: from mechanical activation to mechanically stimulated synthesis

Gudrun Scholz

Summary: This lecture text focuses on the relatively young field of mechanochemistry of fluoride solids, covering both their mechanical activation and their mechanochemical synthesis. The examples provided mainly involve alkaline earth metal compounds, which have interesting potential applications in the field of fluoride ion conductivity or luminescence properties.

CHEMTEXTS (2021)

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Review Chemistry, Multidisciplinary

Mechanochemistry for Synthesis

Tomislav Friscic et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

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Article Chemistry, Multidisciplinary

Mechanochemical Synthesis of Functionalized Quinolines by Iodine Mediated Oxidative Annulation

Atreyee Halder et al.

CHEMISTRY-AN ASIAN JOURNAL (2020)

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Review Chemistry, Multidisciplinary

Recent Advances in the Application of Selectfluor as a Fluorine-free Functional Reagent in Organic Synthesis

Ke Yang et al.

CHEMISTRY-AN ASIAN JOURNAL (2020)

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Article Chemistry, Organic

Solvent-Free and Liquid-Phase Iodination of Thiophene Derivatives with Potassium Dichloroiodate Monohydrate

Grigoriy Sereda et al.

SYNTHESIS-STUTTGART (2020)

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Review Chemistry, Multidisciplinary

Tailor-Made Amino Acids and Fluorinated Motifs as Prominent Traits in Modern Pharmaceuticals

Haibo Mei et al.

CHEMISTRY-A EUROPEAN JOURNAL (2020)

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Article Chemistry, Multidisciplinary

Selective Mechanochemical Monoarylation of Unbiased Dibromoarenes by in Situ Crystallization

Tamae Seo et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2020)

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Article Chemistry, Multidisciplinary

The Use of Copper and Vanadium Mineral Ores in Catalyzed Mechanochemical Carbon-Carbon Bond Formations

Francesco Puccetti et al.

ACS SUSTAINABLE CHEMISTRY & ENGINEERING (2020)

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Article Chemistry, Multidisciplinary

Mechanochemical and Mechanoenzymatic Synthesis of Pharmacologically Active Compounds: A Green Perspective

Mario Perez-Venegas et al.

ACS SUSTAINABLE CHEMISTRY & ENGINEERING (2020)

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Review Biochemistry & Molecular Biology

Novel Methodologies for Chemical Activation in Organic Synthesis under Solvent-Free Reaction Conditions

Claudia Gabriela Avila-Ortiz et al.

MOLECULES (2020)

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Article Chemistry, Multidisciplinary

Mechanochemically Activated Asymmetric Organocatalytic Domino Mannich Reaction-Fluorination

Dominika Kristofikova et al.

ACS SUSTAINABLE CHEMISTRY & ENGINEERING (2020)

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Article Chemistry, Organic

Mechanochemical Synthesis of 1,2,6-Thiadiazine 1-Oxides from Sulfonimidamides and the Fluorescence Properties of the Products

Jan-Hendrik Schoebel et al.

JOURNAL OF ORGANIC CHEMISTRY (2020)

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Article Chemistry, Multidisciplinary

Mechanochemically Induced Chalcogenation of Bicyclic Arenes under Solvent-, Ligand-, Metal-, and Oxidant-Free Conditions

Subir Panja et al.

CHEMISTRYSELECT (2020)

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Article Chemistry, Organic

Halogen effect on enhanced mechanofluorochromic properties of AIE-active tetraphenylethylene-based acylhydrazone luminophores

Junhui Jia et al.

TETRAHEDRON LETTERS (2020)

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Review Chemistry, Multidisciplinary

Ball milling: an efficient and green approach for asymmetric organic syntheses

Ilya N. Egorov et al.

GREEN CHEMISTRY (2020)

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Review Chemistry, Multidisciplinary

Progress and prospects in the use of photocatalysis for the synthesis of organofluorine compounds

Gennady I. Borodkin et al.

RUSSIAN CHEMICAL REVIEWS (2019)

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Editorial Material Biotechnology & Applied Microbiology

Breaking the state-of-the-art in the chemical industry with new-to-Nature products via synthetic microbiology

Laura Martinelli et al.

MICROBIAL BIOTECHNOLOGY (2019)

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Article Chemistry, Multidisciplinary

Methane to Chloromethane by Mechanochemical Activation: A Selective Radical Pathway

Marius Bilke et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2019)

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Article Chemistry, Organic

Hypervalent Iodine Mediated Efficient Solvent-Free Regioselective Halogenation and Thiocyanation of Fused N-Heterocycles

Divakar Reddy Indukuri et al.

SYNLETT (2019)

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Review Biochemistry & Molecular Biology

Recent advances in the synthetic and medicinal perspective of quinolones: A review

Prashant Dhiman et al.

BIOORGANIC CHEMISTRY (2019)

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Review Chemistry, Organic

A Review on Solvent-free Methods in Organic Synthesis

Sainath Zangade et al.

CURRENT ORGANIC CHEMISTRY (2019)

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Article Chemistry, Inorganic & Nuclear

Direct electrophilic fluorination of naproxen with NF-reagents

Gennady I. Borodkin et al.

JOURNAL OF FLUORINE CHEMISTRY (2019)

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Review Chemistry, Organic

Recent developments in C-H functionalization via C-H bond activation using ball milling and transition-metal catalysts

Brindaban C. Ranu et al.

ARKIVOC (2019)

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Article Chemistry, Organic

Palladium-catalyzed ortho-halogenations of acetanilides with N-halosuccinimides via direct sp(2) C-H bond activation in ball mills

Zi Liu et al.

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY (2018)

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Article Chemistry, Organic

Synthesis of 3-Iodobenzofurans by Electrophilic Cyclization under Solventless Conditions in a Ball Mill

Anderson C. Mantovani et al.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2018)

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Review Chemistry, Multidisciplinary

The Green ChemisTREE: 20 years after taking root with the 12 principles

Hanno C. Erythropel et al.

GREEN CHEMISTRY (2018)

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Review Biochemistry & Molecular Biology

Ball Milling Promoted N-Heterocycles Synthesis

Taghreed H. El-Sayed et al.

MOLECULES (2018)

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Article Chemistry, Organic

Dihalogen and Solvent-Free Preparation of syn-Bimane

Ishita Neogi et al.

SYNLETT (2018)

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Article Chemistry, Organic

Mechanochemical Organic Synthesis: The Art of Making Chemistry Green

Vjekoslav Strukil

SYNLETT (2018)

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Article Chemistry, Organic

Mechanochemical electrophilic fluorination of liquid beta-ketoesters

Joseph L. Howard et al.

TETRAHEDRON (2018)

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Article Chemistry, Organic

Recent advances in mechanochemical C-H functionalization reactions

Shujuan Zhao et al.

TETRAHEDRON LETTERS (2018)

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Article Chemistry, Multidisciplinary

Mechanochemistry as an emerging tool for molecular synthesis: what can it offer?

Joseph L. Howard et al.

CHEMICAL SCIENCE (2018)

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Article Chemistry, Multidisciplinary

Fluorine-18: an untapped resource in inorganic chemistry

Cassis Varlow et al.

CHEMICAL COMMUNICATIONS (2018)

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Article Chemistry, Multidisciplinary

Translating solid state organic synthesis from a mixer mill to a continuous twin screw extruder

Qun Cao et al.

GREEN CHEMISTRY (2018)

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Article Chemistry, Organic

Promotional effect of ionic liquids in the electrophilic fluorination of phenols

Gennady I. Borodkin et al.

ARKIVOC (2018)

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Article Chemistry, Organic

Solvent-Free Fluorination of Electron-Rich Aromatic Compounds with F-TEDA-BF4: Toward Dry Processes

Pavel A. Zaikin et al.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2017)

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Review Chemistry, Multidisciplinary

Recent progress on fluorination in aqueous media

Lian Yang et al.

GREEN CHEMISTRY (2017)

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Article Chemistry, Multidisciplinary

An efficient approach for the synthesis of 5-hydroxy-chromeno[2,3-b]pyridines under catalyst and solvent free conditions

Shruti Gupta et al.

GREEN CHEMISTRY (2017)

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Article Chemistry, Multidisciplinary

Fast, solvent-free and highly enantioselective fluorination of β-keto esters catalyzed by chiral copper complexes in a ball mill

Yifeng Wang et al.

GREEN CHEMISTRY (2017)

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Article Chemistry, Multidisciplinary

Controlling reactivity through liquid assisted grinding: the curious case of mechanochemical fluorination

Joseph L. Howard et al.

GREEN CHEMISTRY (2017)

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Article Chemistry, Organic

The application of perfluoroheteroaromatic reagents in the preparation of modified peptide systems

Diana Gimenez et al.

ORGANIC & BIOMOLECULAR CHEMISTRY (2017)

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Review Chemistry, Organic

Synthesis of Antitumor Fluorinated Pyrimidine Nucleosides

Patrizia Ferraboschi et al.

ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL (2017)

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Article Chemistry, Organic

Chemistry 2.0: Developing a New, Solvent-Free System of Chemical Synthesis Based on Mechanochemistry

Jean-Louis Do et al.

SYNLETT (2017)

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Article Chemistry, Multidisciplinary

Catalytic formation of C(sp3)-F bonds via decarboxylative fluorination with mechanochemically-prepared Ag2O/TiO2 heterogeneous catalysts

G. Tarantino et al.

RSC ADVANCES (2017)

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Review Chemistry, Organic

Mechanochemical synthesis of small organic molecules

Tapas Kumar Achar et al.

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY (2017)

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Article Chemistry, Multidisciplinary

C-H Bond Functionalization by Mechanochemistry

Jose G. Hernandez

CHEMISTRY-A EUROPEAN JOURNAL (2017)

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Article Chemistry, Organic

One-pot multistep mechanochemical synthesis of fluorinated pyrazolones

Joseph L. Howard et al.

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY (2017)

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Review Chemistry, Multidisciplinary

Quantum Chemical Strain Analysis For Mechanochemical Processes

Tim Stauch et al.

ACCOUNTS OF CHEMICAL RESEARCH (2017)

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Review Chemistry, Multidisciplinary

Next Generation of Fluorine-Containing Pharmaceuticals, Compounds Currently in Phase II-III Clinical Trials of Major Pharmaceutical Companies: New Structural Trends and Therapeutic Areas

Yu Zhou et al.

CHEMICAL REVIEWS (2016)

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Review Chemistry, Multidisciplinary

18F-Labeling of Arenes and Heteroarenes for Applications in Positron Emission Tomography

Sean Preshlock et al.

CHEMICAL REVIEWS (2016)

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Article Chemistry, Multidisciplinary

Reaction rates in a theory of mechanochemical pathways

Wolfgang Quapp et al.

JOURNAL OF COMPUTATIONAL CHEMISTRY (2016)

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Article Chemistry, Organic

Mechanochemical solid-state synthesis of 2-aminothiazoles, quinoxalines and benzoylbenzofurans from ketones by one-pot sequential acid- and base-mediated reactions

Honnappa Nagarajaiah et al.

ORGANIC & BIOMOLECULAR CHEMISTRY (2016)

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Article Chemistry, Multidisciplinary

Structure Elucidation and Characterization of Different Thyroxine Polymorphs

Santanu Mondal et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2015)

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Article Chemistry, Multidisciplinary

Mechanochemical synthesis of advanced nanomaterials for catalytic applications

Chunping Xu et al.

CHEMICAL COMMUNICATIONS (2015)

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Article Chemistry, Multidisciplinary

[Cp*RhCl2](2): mechanosynthesis and applications in C-H bond functionalisations under ball-milling conditions

Jose G. Hernandez et al.

CHEMICAL COMMUNICATIONS (2015)

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Article Chemistry, Organic

Trihaloisocyanuric Acids as Atom-Economic Reagents for Halogenation of Aromatics and Carbonyl Compounds in the Solid State by Ball Milling

Abhaya K. Mishra et al.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2015)

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Review Chemistry, Multidisciplinary

Fluorine in Pharmaceutical Industry: Fluorine-Containing Drugs Introduced to the Market in the Last Decade (2001-2011)

Jiang Wang et al.

CHEMICAL REVIEWS (2014)

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Review Chemistry, Multidisciplinary

Solvent-Free and Catalysts-Free Chemistry: A Benign Pathway to Sustainability

Manoj B. Gawande et al.

CHEMSUSCHEM (2014)

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Article Chemistry, Organic

Electron-Rich Aromatics Under Ball Milling: Oxidative Aryl-iodination Using I2-Oxone and Biarylation with I2

Saikat Maiti et al.

SYNTHETIC COMMUNICATIONS (2014)

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Article Chemistry, Organic

Electrophilic aryl-halogenation using N-halosuccinimides under ball-milling

Anima Bose et al.

TETRAHEDRON LETTERS (2014)

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Article Chemistry, Organic

Aryl diazonium nanomagnetic sulfate and potassium iodide: an iodination process

Eskandar Kolvari et al.

TETRAHEDRON LETTERS (2014)

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Review Chemistry, Organic

Xenon difluoride in the organic laboratory: a tale of substrates, solvents and vessels

Christopher A. Ramsden

ARKIVOC (2014)

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Review Chemistry, Multidisciplinary

On the mechanochemical activation by ultrasound

Giancarlo Cravotto et al.

CHEMICAL SOCIETY REVIEWS (2013)

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Review Chemistry, Multidisciplinary

The historical development of mechanochemistry

Laszlo Takacs

CHEMICAL SOCIETY REVIEWS (2013)

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News Item Chemistry, Multidisciplinary

MECHANOCHEMICAL SYNTHESIS How grinding evolves

Kenneth D. M. Harris

NATURE CHEMISTRY (2013)

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Article Chemistry, Organic

Solvent-free mechanochernical chlorination of hydrocarbons with CuCl2

Jozef Visnovsky et al.

TETRAHEDRON LETTERS (2013)

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Article Chemistry, Organic

Synthesis of a novel tetrafluoropyridine-containing amino acid and tripeptide

Alex S. Hudson et al.

TETRAHEDRON LETTERS (2013)

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Article Chemistry, Multidisciplinary

Aromatic substitution in ball mills: formation of aryl chlorides and bromides using potassium peroxomonosulfate and NaX

Robert Schmidt et al.

GREEN CHEMISTRY (2012)

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Article Chemistry, Multidisciplinary

Solvent-free bromination reactions with sodium bromide and oxone promoted by mechanical milling

Guan-Wu Wang et al.

GREEN CHEMISTRY (2012)

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Article Chemistry, Inorganic & Nuclear

Selective elemental fluorination in ionic liquids

M. E. Hirschberg et al.

JOURNAL OF FLUORINE CHEMISTRY (2012)

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Review Chemistry, Applied

Selective Continuous Flow Processes Using Fluorine Gas

Christopher B. McPake et al.

ORGANIC PROCESS RESEARCH & DEVELOPMENT (2012)

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Review Pharmacology & Pharmacy

Bioactivation of Drugs: Risk and Drug Design

John S. Walsh et al.

ANNUAL REVIEW OF PHARMACOLOGY AND TOXICOLOGY, VOL 51, 2011 (2011)

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Review Chemistry, Inorganic & Nuclear

Fluorinated azines and benzazines containing oxygen or sulfur atoms

E. V. Nosova et al.

JOURNAL OF FLUORINE CHEMISTRY (2010)

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Article Biochemistry & Molecular Biology

The role of fluorine in medicinal chemistry

Poonam Shah et al.

JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY (2007)

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Review Chemistry, Organic

Electrophilic reactions of aromatic and heteroaromatic compounds in ionic liquids

G. I. Borodkin et al.

RUSSIAN JOURNAL OF ORGANIC CHEMISTRY (2006)

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Article Chemistry, Multidisciplinary

Atom efficiency and catalysis in organic synthesis

RA Sheldon

PURE AND APPLIED CHEMISTRY (2000)

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