☆ 4.6 Article

Synthesis of Sulfonyl, Sulfonimidoyl, and Sulfoxyl Fluorides under Solvent-Free Mechanochemical Conditions in a Mixer Mill by Imidazole-to-Fluorine Exchange

ACS SUSTAINABLE CHEMISTRY & ENGINEERING (2023)

Related references

Note: Only part of the references are listed.
Article Chemistry, Physical

Electro-mechanochemical approach towards the chloro sulfoximidations of allenes under solvent-free conditions in a ball mill

Mostafa M. Amer et al.

Summary: An electro-mechanochemical protocol using strained BaTiO3 nanoparticles has been developed for the synthesis of vinylic sulfoximines. The catalytic active system is generated in situ by the reduction of copper(ii) chloride. The method tolerates various electron-donating and -withdrawing groups, and leads to difunctionalised double bond products in good to excellent yields. Attempts to add a sulfoximidoyl chloride to an alkyne were difficult, while additions of a sulfonyl iodide to allenes and alkynes proceeded smoothly in the presence of silica gel without needing activation by a piezoelectric material.

FARADAY DISCUSSIONS (2023)

Add to Collection
Article Chemistry, Multidisciplinary

Mechanochemically-Assisted Synthesis of Polyimides

Tilo Rensch et al.

Summary: Polyimides were synthesized with a high yield in under 1 hour using a beat and heat approach, involving solvent-free vibrational ball milling and thermal treatment, exploring various additives and conducting quantum chemical calculations. Water removal was identified as the crucial step in the reaction mechanism, making this method significantly faster and more versatile than traditional solution-based processes.

CHEMSUSCHEM (2022)

Add to Collection
Article Chemistry, Multidisciplinary

Solid-State C-N Cross-Coupling Reactions with Carbazoles as Nitrogen Nucleophiles Using Mechanochemistry

Koji Kubota et al.

Summary: The study presents a palladium-catalyzed solid-state C-N cross-coupling of carbazoles with aryl halides via a high-temperature ball-milling technique, allowing for the efficient synthesis of N-arylcarbazole derivatives without the use of large amounts of organic solvents. Importantly, this method enables the coupling of poorly soluble aryl halides with large polyaromatic structures that are barely reactive under conventional solution-based conditions.

CHEMSUSCHEM (2022)

Add to Collection
Article Chemistry, Multidisciplinary

Efficient access to materials-oriented aromatic alkynes via the mechanochemical Sonogashira coupling of solid aryl halides with large polycyclic conjugated systems

Yunpeng Gao et al.

Summary: The study demonstrates the efficient palladium-catalyzed Sonogashira coupling of solid aryl halides using high-temperature ball milling, resulting in a variety of materials-oriented polyaromatic alkynes and the synthesis of novel luminescent materials. The utility of this method is further exemplified by the rapid synthesis of a fluorescent metal-organic framework precursor, showcasing the potential of Sonogashira coupling for the preparation of functional materials.

CHEMICAL SCIENCE (2022)

Add to Collection
Review Chemistry, Multidisciplinary

The Mechanochemical Synthesis and Activation of Carbon-Rich π-Conjugated Materials

Mingjun Xuan et al.

Summary: Mechanochemistry uses mechanical force to break, form, and manipulate chemical bonds to achieve functional transformations and syntheses. Many innovative applications of mechanochemistry have been developed in recent years, particularly in the synthesis and activation of carbon-rich pi-conjugated materials. This review summarizes the recent advances in this research field, combining the viewpoints of polymer and trituration mechanochemistry, focusing on optical force probes, the force-induced release of small dye molecules, and the mechanochemical synthesis of polyacetylene, carbon allotropes, and other pi-conjugated materials.

ADVANCED SCIENCE (2022)

Add to Collection
Article Chemistry, Multidisciplinary

Mechanochemical Solvent-Free N-Sulfenylations of Sulfoximines and Sulfonimidamides

Deshen Kong et al.

Summary: Mechanochemical N-sulfenylations of sulfoximines and sulfonimidamides mediated by silver oxide under solvent-free conditions have been developed. The reactions are easy to perform, proceed well on a gram scale, and tolerate a wide range of functional groups in the substrates. Compared to its solvent-based counterpart, the mechanochemical approach shows significant ecological advantages.

ACS SUSTAINABLE CHEMISTRY & ENGINEERING (2022)

Add to Collection
Article Chemistry, Organic

Acid-Mediated Imidazole-to-Fluorine Exchange for the Synthesis of Sulfonyl and Sulfonimidoyl Fluorides

Marco T. Passia et al.

Summary: A simple method for the preparation of sulfur(VI) fluorides using sulfonyl imidazoles as starting materials was described. The exchange reaction between imidazoles and fluorine resulted in a variety of sulfur(VI) fluorides with good yields.

ORGANIC LETTERS (2022)

Add to Collection
Review Chemistry, Multidisciplinary

New Opportunities for the Utilization of the Sulfoximine Group in Medicinal Chemistry from the Drug Designer's Perspective

Ulrich Luecking

Summary: This article highlights the emerging trends and opportunities for drug designers to utilize the sulfoximine group in medicinal chemistry, such as in the construction of complex molecules, PROTACs, ADCs, and novel warheads for covalent inhibition. Despite the increasing interest in the sulfoximine group in recent years, there is still ample room for further innovative applications.

CHEMISTRY-A EUROPEAN JOURNAL (2022)

Add to Collection
Review Chemistry, Multidisciplinary

Mechanochemistry: New Tools to Navigate the Uncharted Territory of Impossible Reactions

Federico Cuccu et al.

Summary: Mechanochemical transformations have revolutionized the field of chemistry, particularly in organic synthesis, by challenging traditional concepts and opening up new reaction paths.

CHEMSUSCHEM (2022)

Add to Collection
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)

Add to Collection
Article Chemistry, Multidisciplinary

Stainless steel-initiated thiosulfonylations of unactivated alkenes under solvent-free conditions in a mixer mill

Deshen Kong et al.

Summary: Thiosulfonates can be added to unactivated alkenes under solvent-free conditions, using a mixer mill made of stainless steel. This thiosulfonylation reaction tolerates a wide range of functional groups and leads to high product yields in short reaction times.

GREEN CHEMISTRY (2022)

Add to Collection
Article Chemistry, Multidisciplinary

Stainless steel-initiated chloro sulfoximidations of allenes under solvent-free conditions in a ball mill

Deshen Kong et al.

Summary: In this study, mechanochemical regioselective chloro sulfoximidations of allenes were achieved through stainless steel-initiated radical addition reactions at ambient temperature under solvent-free conditions. The reactions showed good compatibility with a wide range of substrates and did not require an additional catalyst. The resulting vinyl sulfoximines were found to be further derivatizable. Similar reactions were also observed with arylsulfonyl iodides adding to allenes.

GREEN CHEMISTRY (2022)

Add to Collection
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)

Add to Collection
Article Chemistry, Multidisciplinary

Syntheses and Transformations of Sulfoximines

Wenting Zheng et al.

Summary: Sulfoximines are versatile compounds that are widely used in various fields, and can be synthesized and transformed in different ways, showing great potential for a wide range of applications.

CHEMICAL RECORD (2021)

Add to Collection
Review Chemistry, Medicinal

Application of sulfoximines in medicinal chemistry from 2013 to 2020

Yu Han et al.

Summary: Interest in sulfoximine chemistry has increased in recent years, with several sulfoximine-containing drugs entering clinical trials. However, limited experience in physicochemical and in vitro parameters of sulfoximines hampers their routine application in drug discovery. This review aims to provide support for the addition of sulfoximine components in medicinal chemists' toolbox.

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY (2021)

Add to Collection
Article Chemistry, Multidisciplinary

Fullerene Mechanochemistry: Serendipitous Discovery of Dumb-Bell-Shaped C120 and Beyond

Guan-Wu Wang

Summary: The article describes the serendipitous discovery of dumb-bell-shaped C-120 under high-speed vibration milling conditions and the use of mechanochemical protocol for synthesizing various fullerene compounds. The author shares his experience of getting into mechanochemical reactions of fullerenes and discovering the fullerene dimer C-120. He emphasizes scientific rigor and intolerance of research misconduct with his students, as well as guiding them through scientific work.

CHINESE JOURNAL OF CHEMISTRY (2021)

Add to Collection
Article Chemistry, Physical

Palladium-Catalyzed Solid-State Polyfluoroarylation of Aryl Halides Using Mechanochemistry

Rikuro Takahashi et al.

Summary: The palladium-catalyzed cross-coupling under solid-state high temperature ball-milling conditions enables efficient construction of polyfluorinated structural motifs without the need for stoichiometric additives, large amounts of organic solvents, and exhibits a broad substrate scope.

ACS CATALYSIS (2021)

Add to Collection
Article Chemistry, Multidisciplinary

Mechanoredox Chemistry as an Emerging Strategy in Synthesis

Jamie A. Leitch et al.

Summary: Recent research has shown that mechanochemical activation of piezoelectric materials can open new avenues in redox chemistry, mimicking established photoredox catalytic cycles. Proof-of-concept studies have demonstrated that mechanoredox chemistry holds great potential in sustainable and efficient radical-based synthesis.

CHEMISTRY-A EUROPEAN JOURNAL (2021)

Add to Collection
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)

Add to Collection
Article Chemistry, Multidisciplinary

Tackling Solubility Issues in Organic Synthesis: Solid-State Cross-Coupling of Insoluble Aryl Halides

Tamae Seo et al.

Summary: The study presents a fast and efficient solid-state method for Suzuki-Miyaura cross-coupling reactions that can handle reactions which are not feasible under traditional solution conditions. A new luminescent organic material with strong red emission was discovered and successfully prepared through molecular transformations.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2021)

Add to Collection
Article Chemistry, Organic

2,3-Dihydro-1,2,6-thiadiazine 1-Oxides by Biginelli-Type Reactions with Sulfonimidamides under Mechanochemical Conditions

Felix Krauskopf et al.

Summary: In this study, 2,3-dihydro-1,2,6-thiadiazine 1-oxides were synthesized in high yields through Biginelli-type multicomponent reactions using NH-free sulfonimidamides under solvent-free mechanochemical conditions, with acetic acid or ytterbium triflate as catalysts. Characterization of a representative product by X-ray single crystal structure analysis revealed molecular details of the highly functionalized three-dimensional heterocycle, leading to the discovery of additional structural scaffolds through further product modifications.

ORGANIC LETTERS (2021)

Add to Collection
Review Chemistry, Multidisciplinary

Synthesis and Transformations of NH-Sulfoximines

Michael Andresini et al.

Summary: In recent years, there has been a significant increase in the use of sulfoximines in the field of chemistry, as they are considered valuable motifs in medicinal chemistry, due to pioneering works in clinical trials and the development of synthetic methods. Recent developments in sulfoximine synthesis, focusing on S-N and S-C bond formations since 2015, as well as the use of flow chemistry processes and subsequent transformations, particularly in N-functionalization, have been covered in this review.

CHEMISTRY-A EUROPEAN JOURNAL (2021)

Add to Collection
Editorial Material Pharmacology & Pharmacy

How do we address neglected sulfur pharmacophores in drug discovery?

Michael J. Tilby et al.

EXPERT OPINION ON DRUG DISCOVERY (2021)

Add to Collection
Article Chemistry, Organic

Mechanochemical Rearrangements

David Virieux et al.

Summary: Molecular rearrangements using mechanochemistry are a powerful tool to construct complex structures in a sustainable manner, particularly for preparing active pharmaceutical ingredients and natural products. This approach, although still in its early stages, holds promise for chemists to merge molecular diversity and green chemistry perspectives towards more selective and efficient syntheses.

JOURNAL OF ORGANIC CHEMISTRY (2021)

Add to Collection
Article Chemistry, Organic

Synthesis of trifluoromethyl-substituted 1,2,6-thiadiazine 1-oxides from sulfonimidamides under mechanochemical conditions

Marco Thomas Passia et al.

Summary: In this study, TBS-protected or NH-sulfonimidamides were reacted with beta-alkoxyvinyl trifluoromethylketones under solvent-free mechanochemical conditions to produce 3-trifluoromethyl-substituted three-dimensional 1,2,6-thiadiazine 1-oxides. C4-functionalized products were obtained by starting from cyclic enones and brominations of the initially formed heterocycles. The stability of the products was investigated by varying the pH value and storage under aerobic conditions.

ORGANIC & BIOMOLECULAR CHEMISTRY (2021)

Add to Collection
Review Chemistry, Multidisciplinary

Mechanochemistry for Synthesis

Tomislav Friscic et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

Add to Collection
Article Chemistry, Multidisciplinary

Greener Dye Synthesis: Continuous, Solvent-Free Synthesis of Commodity Perylene Diimides by Twin-Screw Extrusion

Qun Cao et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

Add to Collection
Article Chemistry, Multidisciplinary

Mechanochemical Palladium-Catalyzed Carbonylative Reactions Using Mo(CO)6

Pit van Bonn et al.

CHEMISTRY-A EUROPEAN JOURNAL (2020)

Add to Collection
Review Chemistry, Multidisciplinary

Direct Mechanocatalysis: Using Milling Balls as Catalysts

Wilm Pickhardt et al.

CHEMISTRY-A EUROPEAN JOURNAL (2020)

Add to Collection
Review Chemistry, Physical

Metal-Mediated and Metal-Catalyzed Reactions Under Mechanochemical Conditions

Andrea Porcheddu et al.

ACS CATALYSIS (2020)

Add to Collection
Article Chemistry, Multidisciplinary

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

Mario Perez-Venegas et al.

ACS SUSTAINABLE CHEMISTRY & ENGINEERING (2020)

Add to Collection
Article Chemistry, Medicinal

Sulfoximines as Rising Stars in Modern Drug Discovery? Current Status and Perspective on an Emerging Functional Group in Medicinal Chemistry

Patrick Maeder et al.

JOURNAL OF MEDICINAL CHEMISTRY (2020)

Add to Collection
Review Chemistry, Organic

N-H and C-H Functionalization of Sulfoximine: Recent Advancement and Prospects

Prasanjit Ghosh et al.

ASIAN JOURNAL OF ORGANIC CHEMISTRY (2020)

Add to Collection
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)

Add to Collection
Article Chemistry, Organic

N-(2,3,5,6-Tetrafluoropyridyl)sulfoximines: synthesis, X-ray crystallography, and halogen bonding

Christian Schumacher et al.

ORGANIC CHEMISTRY FRONTIERS (2020)

Add to Collection
Review Chemistry, Multidisciplinary

Mechanochemical Cross-Coupling Reactions

Koji Kubota et al.

TRENDS IN CHEMISTRY (2020)

Add to Collection
Review Biochemistry & Molecular Biology

Construction of sulfur-containing moieties in the total synthesis of natural products

Nengzhong Wang et al.

NATURAL PRODUCT REPORTS (2020)

Add to Collection
Review Chemistry, Multidisciplinary

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

Ilya N. Egorov et al.

GREEN CHEMISTRY (2020)

Add to Collection
Review Chemistry, Multidisciplinary

Mechanochemistry of Gaseous Reactants

Carsten Bolm et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019)

Add to Collection
Review Chemistry, Multidisciplinary

The growing applications of SuFEx click chemistry

A. S. Barrow et al.

CHEMICAL SOCIETY REVIEWS (2019)

Add to Collection
Article Chemistry, Multidisciplinary

Exploration of Novel Chemical Space: Synthesis and in vitro Evaluation of N-Functionalized Tertiary Sulfonimidamides

Flavia Izzo et al.

CHEMISTRY-A EUROPEAN JOURNAL (2018)

Add to Collection
Review Chemistry, Organic

Sulfonyl Fluorides (SFs): More Than Click Reagents?

Praveen K. Chinthakindi et al.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2018)

Add to Collection
Article Chemistry, Multidisciplinary

Transition-metal-catalyzed C-N cross-coupling reactions of N-unsubstituted sulfoximines: a review

Akram Hosseinian et al.

JOURNAL OF SULFUR CHEMISTRY (2018)

Add to Collection
Article Polymer Science

Highly efficient polymerization via sulfur(VI)-fluoride exchange (SuFEx): novel polysulfates bearing a pyrazoline-naphthylamide conjugated moiety and their electrical memory performance

Xiong Xiao et al.

POLYMER CHEMISTRY (2018)

Add to Collection
Article Chemistry, Multidisciplinary

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

Joseph L. Howard et al.

CHEMICAL SCIENCE (2018)

Add to Collection
Editorial Material Chemistry, Medicinal

Emerging Utility of Fluorosulfate Chemical Probes

Lyn H. Jones

ACS MEDICINAL CHEMISTRY LETTERS (2018)

Add to Collection
Review Chemistry, Organic

Synthesis and Chemical Transformations of Fluorosulfates

Lekkala Revathi et al.

ASIAN JOURNAL OF ORGANIC CHEMISTRY (2018)

Add to Collection
Review Chemistry, Multidisciplinary

Analysis of US FDA-Approved Drugs Containing Sulfur Atoms

Kevin A. Scott et al.

TOPICS IN CURRENT CHEMISTRY (2018)

Add to Collection
Review Chemistry, Applied

Sulfonimidamides: Synthesis and Applications in Preparative Organic Chemistry

Ganesh Chandra Nandi et al.

ADVANCED SYNTHESIS & CATALYSIS (2018)

Add to Collection
Review Chemistry, Inorganic & Nuclear

Recent advances towards sulfur (VI) fluoride exchange (SuFEx) click chemistry

Tanzeela Abdul Fattah et al.

JOURNAL OF FLUORINE CHEMISTRY (2018)

Add to Collection
Article Chemistry, Multidisciplinary

Facile Synthesis of Sequence-Regulated Synthetic Polymers Using Orthogonal SuFEx and CuAAC Click Reactions

Cangjie Yang et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2018)

Add to Collection
Article Chemistry, Multidisciplinary

Mechanochemistry: A Force of Synthesis

Jean-Louis Do et al.

ACS CENTRAL SCIENCE (2017)

Add to Collection
Article Chemistry, Medicinal

Sulfoximines from a Medicinal Chemist's Perspective: Physicochemical and in vitro Parameters Relevant for Drug Discovery

Marcus Frings et al.

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY (2017)

Add to Collection
Article Chemistry, Organic

Altering Product Selectivity by Mechanochemistry

Jose G. Hernandez et al.

JOURNAL OF ORGANIC CHEMISTRY (2017)

Add to Collection
Article Chemistry, Multidisciplinary

SuFEx-Based Polysulfonate Formation from Ethenesulfonyl Fluoride-Amine Adducts

Hua Wang et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2017)

Add to Collection
Review Chemistry, Applied

Recent Advances in Organic Reactions Involving Elemental Sulfur

Thanh Binh Nguyen

ADVANCED SYNTHESIS & CATALYSIS (2017)

Add to Collection
Article Chemistry, Multidisciplinary

PyFluor: A Low-Cost, Stable, and Selective Deoxyfluorination Reagent

Matthew K. Nielsen et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2015)

Add to Collection
Article Chemistry, Inorganic & Nuclear

THE SIGNIFICANCE OF ORGANOSULFUR COMPOUNDS IN CROP PROTECTION: CURRENT EXAMPLES FROM FUNGICIDE RESEARCH

Clemens Lamberth et al.

PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS (2015)

Add to Collection
Review Chemistry, Multidisciplinary

Sulfur(VI) Fluoride Exchange (SuFEx): Another Good Reaction for Click Chemistry

Jiajia Dong et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2014)

Add to Collection
Review Chemistry, Multidisciplinary

Fluorinated sulfoximines: syntheses, properties and applications

Vincent Bizet et al.

CHEMICAL SOCIETY REVIEWS (2014)

Add to Collection
Article Chemistry, Medicinal

Data-Mining for Sulfur and Fluorine: An Evaluation of Pharmaceuticals To Reveal Opportunities for Drug Design and Discovery

Elizabeth A. Ilardi et al.

JOURNAL OF MEDICINAL CHEMISTRY (2014)

Add to Collection
Article Chemistry, Organic

Ascertaining the Suitability of Aryl Sulfonyl Fluorides for [18F]Radiochemistry Applications: A Systematic Investigation using Microfluidics

Lidia Matesic et al.

JOURNAL OF ORGANIC CHEMISTRY (2013)

Add to Collection
Review Chemistry, Multidisciplinary

Mechanochemistry: opportunities for new and cleaner synthesis

Stuart L. James et al.

CHEMICAL SOCIETY REVIEWS (2012)

Add to Collection
Article Chemistry, Multidisciplinary

Sulfonyl Fluoride-Based Prosthetic Compounds as Potential 18F Labelling Agents

James A. H. Inkster et al.

CHEMISTRY-A EUROPEAN JOURNAL (2012)

Add to Collection
Webinars Posters Questions Hubs Funding Journals Papers Connect Collections Reviewers About Us FAQs Mobile App Privacy Policy Terms of Use
© Peeref 2019-2024. All rights reserved.