4.8 Article

Selective Fluorosulfonylation of Thianthrenium Salts Enabled by Electrochemistry

相关参考文献

注意:仅列出部分参考文献,下载原文获取全部文献信息。
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)

Article Chemistry, Organic

Cyanation and cyanomethylation of trimethylammonium salts via electrochemical cleavage of C-N bonds

Xianqiang Kong et al.

Summary: A practical and mild electrochemical protocol has been developed for cyanation and cyanomethylation of trimethylammonium salts through C-N bond cleavage without the need for external stoichiometric reducing agents or sacrificial anodes. The reaction shows high functional group compatibility and can be used for the synthesis of natural product derivatives. Preliminary mechanistic studies suggest the involvement of a radical addition pathway.

ORGANIC CHEMISTRY FRONTIERS (2022)

Article Chemistry, Organic

Aliphatic sulfonyl fluoride synthesis via reductive decarboxylative fluorosulfonylation of aliphatic carboxylic acid NHPI esters

Zhanhu Ma et al.

Summary: By utilizing a radical sulfur dioxide insertion and fluorination strategy, we have successfully developed an efficient method for synthesizing aliphatic sulfonyl fluorides. This method utilizes readily available carboxylic acids, a reductant, a sulfur dioxide surrogate, and the electrophilic fluorination reagent NFSI under reduction conditions. The protocol allows for the synthesis of various aliphatic sulfonyl fluorides and is compatible with a wide range of functional groups.

ORGANIC CHEMISTRY FRONTIERS (2022)

Review Chemistry, Multidisciplinary

Sulfonyl fluorides as targets and substrates in the development of new synthetic methods

Terry Shing-Bong Lou et al.

Summary: The advent of sulfur(VI)-fluoride exchange (SuFEx) processes has led to research into electrophilic species featuring a sulfur-fluorine bond. Sulfonyl fluorides, known for their reactivity and stability, have been extensively studied for their applications in medicinal chemistry and chemical biology. Various synthetic approaches, starting from sulfur-containing and non-sulfur-containing substrates, have been developed. This review provides an overview of the challenges and progress in the synthesis and manipulation of sulfonyl fluorides.

NATURE REVIEWS CHEMISTRY (2022)

Article Chemistry, Multidisciplinary

Electrochemical Synthesis of Sulfonyl Fluorides with Triethylamine Hydrofluoride

Lei Zhang et al.

Summary: In this work, the electrochemical synthesis of sulfonyl fluorides using Et3N-3HF as the fluoride source is reported. The reaction allows efficient synthesis of sulfonyl fluorides without the use of external oxidant by combining Et3N-3HF with aryl/alkyl sulfinic salt. Furthermore, the method demonstrates its advantage in a tandem reaction involving Pd-catalyzed C-S cross-coupling and formation of S-F bond, with good tolerance towards a variety of functional groups.

CHINESE JOURNAL OF CHEMISTRY (2022)

Article Chemistry, Organic

Scalable Electrocatalytic Intermolecular Acylcyanation and Aminocyanation of Alkenes

Xianqiang Kong et al.

Summary: An electrocatalytic method for three-component acylcyanation and aminocyanation of simple alkenes has been developed. The protocol exhibits high tolerance towards functional groups and can be easily scaled up. The key to its success lies in the use of an electrophilic cyanation source, which expands the application of alkenes to aliphatic ones in acylcyanation.

JOURNAL OF ORGANIC CHEMISTRY (2022)

Article Chemistry, Organic

A Practically Unified Electrochemical Strategy for Ni-Catalyzed Decarboxylative Cross-Coupling of Aryl Trimethylammonium Salts

Xianqiang Kong et al.

Summary: By combining electrocatalysis and nickel catalysis, a unified strategy has been applied to successfully achieve the decarboxylative cross-coupling of four types of alpha-oxocarboxylic acids and their derivatives with aryl trimethylammonium salts under mild conditions. Our strategy provides a practical way for preparing aryl ketones, amides, esters, or aldehydes.

ORGANIC LETTERS (2022)

Article Chemistry, Organic

Photoredox-Catalyzed?-Sulfonylation of Ketones from SulfurDioxide and Thianthrenium Salts

Fu-Sheng He et al.

Summary: This research developed a new photoredox-catalyzed reaction method, which can introduce various functionalized sulfonyl groups into ketones through the synthesis of easily accessible starting materials and good functional group compatibility. In addition, it is the first time that α-methylsulfonated ketones have been synthesized using methanol as the methyl source, which is an important industrial raw material.

ORGANIC LETTERS (2022)

Article Chemistry, Organic

Electrochemical Synthesis of β-Keto Sulfonyl Fluorides via Radical Fluorosulfonylation of Vinyl Triflates

Qingyuan Feng et al.

Summary: Versatile beta-keto sulfonyl fluorides can be synthesized by electrochemical methods using inexpensive graphite felt as electrodes, without the need for metal catalysts. This protocol offers a mild and scalable approach to access valuable compounds from readily available precursors, including cyclic ones that were previously difficult to obtain.

ORGANIC LETTERS (2022)

Article Chemistry, Multidisciplinary

Radical Hydro-Fluorosulfonylation of Unactivated Alkenes and Alkynes

Peng Wang et al.

Summary: A new method based on radical fluorosulfonylation has been developed for the synthesis of aliphatic sulfonyl fluorides from unactivated alkenes. This method can be applied to the late-stage modifications of natural products and peptides, as well as drug ligation.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2022)

Article Chemistry, Organic

Palladium-Catalyzed Synthesis of Esters from Arenes through C-H Thianthrenation

Mengning Wang et al.

Summary: Efficient palladium-catalyzed synthesis of esters from available arenes has been achieved by regioselective thianthrenation to generate aryl-TT salts, which can couple with phenol formate and N-hydroxysuccinimide formate to form phenol esters and NHS esters, respectively. A wide range of functional esters can be prepared efficiently under this redox-neutral palladium-catalytic condition. The established platform and products show potential for late-stage functionalization and synthetic applications.

ORGANIC LETTERS (2022)

Article Chemistry, Organic

Electrochemical Synthesis of β-Functionalized Ketones via Ring-Opening of Cycloalkanols

Lulu Zhao et al.

Summary: The electrochemical deconstructive functionalization of cycloalkanols with nucleophiles exclusively at the beta-position of ketones has been studied. A wide range of cycloalkanols and different N, O, C, and P-centered nucleophiles were used in this reaction, providing easy access to beta-functionalized ketones as products. The reaction involves the generation of alpha,beta-unsaturated ketones as key intermediates, followed by Michael addition with nucleophiles.

ORGANIC LETTERS (2022)

Article Chemistry, Organic

Palladium-Catalyzed Synthesis of C-1 Deuterated Aldehydes from (Hetero) Arenes Mediated by C (sp2)-H Thianthrenation

Binlin Zhao et al.

Summary: In this study, a palladium-catalyzed method was developed to synthesize structurally diverse C-1 deuterated aldehydes from readily available arenes, achieving deuterium incorporation with high selectivity (96%-99%). The cost-effective DCOONa was used as a convenient deuterium source under palladium-catalytic redox neutral conditions. This catalytic approach enables direct late-stage C-H functionalization of bioactive molecules and natural product derivatives assisted by C(sp(2))-H thianthrenation, and can also be applied to prepare deuterated drugs and analogues with high levels of deuterium incorporation.

ORGANIC LETTERS (2022)

Review Chemistry, Organic

Recent Advances in Thianthrenation/Phenoxathiination Enabled Site-Selective Functionalization of Arenes

Xiao-Yue Chen et al.

Summary: Selective functionalization of simple arenes has been a major challenge due to the similarity of multiple C-H bonds in the same molecule. However, recent research has shown that the use of aryl thianthrenium salts can achieve site-selective C-H functionalization in arenes, providing a promising solution for late-stage functionalization of bioactive molecules.

SYNTHESIS-STUTTGART (2022)

Article Multidisciplinary Sciences

A practical fluorosulfonylating platform via photocatalytic imidazolium-based SO2F radical reagent

Weigang Zhang et al.

Summary: The authors have developed an air-stable fluorosulfonylating reagent that enables the synthesis of a variety of sulfonyl fluoride compounds. This method shows potential application in chemical biology, materials science, and drug discovery.

NATURE COMMUNICATIONS (2022)

Article Chemistry, Multidisciplinary

Intermolecular Metal-Free Cyclopropanation and Aziridination of Alkenes with XH2 (X=N, C) by Thianthrenation

Ming-Shang Liu et al.

Summary: In this study, a metal-free protocol for synthesizing aziridines and cyclopropanes using free XH2 and alkenes is presented. The method allows for direct aziridination and cyclopropanation with unprotected XH2, and offers an attractive alternative for the straightforward synthesis of these compounds from readily available starting materials.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2022)

Review Chemistry, Multidisciplinary

Organothianthrenium salts: synthesis and utilization

Huan Meng et al.

Summary: Organothianthrenium salts are compounds containing a positively charged sulfur atom and a neutral sulfur atom. They have unique structural characteristics and chemical behaviors, making them attractive precursors for forming new C-C and C-X bonds. The thianthrenation strategy allows selective transformation of C-H, C-O, and other chemical bonds into organothianthrenium salts, providing a straightforward alternative for functionalization of different compounds.

CHEMICAL SCIENCE (2022)

Article Chemistry, Multidisciplinary

Nickel(ii)-catalyzed highly selective 1,2-diborylation of non-activated monosubstituted alkenes

Zhi-Kai Zhang et al.

Summary: This article presents a practical method for 1,2-diborylation of non-activated monosubstituted alkenes via nickel catalysis. The method shows high tolerance towards functional groups and can be applied for the synthesis of drugs and modification of natural product derivatives. Preliminary mechanistic studies suggest the involvement of a Ni(ii) catalytic cycle.

CHEMICAL COMMUNICATIONS (2022)

Article Chemistry, Multidisciplinary

Copper-catalyzed direct decarboxylative fluorosulfonylation of aliphatic carboxylic acids

Ji-Tao Yi et al.

Summary: In this study, two efficient and complementary methods for direct decarboxylative fluorosulfonylation of carboxylic acids were reported by combining copper catalysis with different N-centered HAT regents. A wide range of structurally diverse sulfonyl fluorides can be readily accessed from primary, secondary, and tertiary carboxylic acids in a single step under mild conditions.

CHEMICAL COMMUNICATIONS (2022)

Article Chemistry, Multidisciplinary

A general electron donor-acceptor complex for photoactivation of arenes via thianthrenation

Kai Sun et al.

Summary: A new method of photoactivation of electron donor-acceptor complexes between arylsulfonium salts and 1,4-diazabicyclo[2.2.2]octane with visible light or natural sunlight was discovered, enabling the generation of aryl radicals under mild conditions, offering a novel opportunity for two-step para-selective C-H functionalization of complex arenes.

CHEMICAL SCIENCE (2022)

Article Chemistry, Multidisciplinary

Redox-Neutral Organometallic Elementary Steps at Bismuth: Catalytic Synthesis of Aryl Sulfonyl Fluorides

Marc Magre et al.

Summary: A bi-catalyzed synthesis of sulfonyl fluorides from (hetero)aryl boronic acids is demonstrated using organobismuth(III) catalysts, resulting in excellent yields and wide functional group tolerance. The catalytic cycle involves various organometallic steps without changing the oxidation state, forming a structurally unique bismuth sulfinate complex.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2021)

Article Chemistry, Multidisciplinary

Metal-Free Visible-Light Synthesis of Arylsulfonyl Fluorides: Scope and Mechanism

Dan Louvel et al.

Summary: The first metal-free procedure for the synthesis of arylsulfonyl fluorides is reported in this study. The reaction using organo-photoredox conditions allows aryl diazonium salts to react with a readily available SO2 source (DABSO) to afford the desired product through simple nucleophilic fluorination. Experimental techniques such as fluorescence, NMR, and EPR spectroscopy, as well as DFT calculations, were used to shed light on the reaction mechanism.

CHEMISTRY-A EUROPEAN JOURNAL (2021)

Editorial Material Chemistry, Multidisciplinary

Green organic synthesis

Wei-Min He et al.

CHINESE CHEMICAL LETTERS (2021)

Review Chemistry, Multidisciplinary

Recent progress in the synthesis of sulfonyl fluorides for SuFEx click chemistry

Tao Zhong et al.

Summary: The SuFEx reaction introduced in 2014 is an efficient and reliable click chemistry tool for creating modular intermolecular connections, attracting significant attention in various fields. This review focuses on the synthetic methods of sulfonyl fluorides to stimulate the development of more efficient methods in this area.

CHINESE CHEMICAL LETTERS (2021)

Article Chemistry, Multidisciplinary

Introducing A New Class of Sulfonyl Fluoride Hubs via Radical Chloro-Fluorosulfonylation of Alkynes

Xingliang Nie et al.

Summary: Sulfonyl fluorides are widely used in various important fields, and the introduction of a new class of sulfonyl fluoride hub, BCASF, can significantly improve synthetic efficiency and expand the range of available structures. BCASF molecules exhibit versatile reactivities, undergoing various transformations while keeping the sulfonyl fluoride group intact, making them useful in synthesizing challenging sulfonyl fluoride compounds.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

Article Chemistry, Multidisciplinary

Enabling the Use of Alkyl Thianthrenium Salts in Cross-Coupling Reactions by Copper Catalysis

Cheng Chen et al.

Summary: Alkyl thianthrenium salts have been synthesized as reliable alkylation reagents, which can readily engage in copper-catalyzed Sonogashira and Kumada reactions to build C(sp(3))-C(sp) bonds under mild photochemical conditions. The method demonstrates great functional breadth and compatibility, even with sensitive Cl, Br, and I atoms.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

Article Multidisciplinary Sciences

Aziridine synthesis by coupling amines and alkenes via an electrogenerated dication

Dylan E. Holst et al.

Summary: In summary, this study introduces a new synthetic strategy for electrochemically transforming unactivated alkenes into N-alkyl aziridines, expanding the scope of accessible products compared to existing methods.

NATURE (2021)

Article Chemistry, Organic

Photochemical (Hetero-)Arylation of Aryl Sulfonium Salts

Yue Zhao et al.

Summary: The construction of (hetero)biaryls through a photoinduced and catalyst-free C-H/C-H cross-coupling provides a simple and efficient synthetic approach by selectively forming aryl thianthrenium salts. Using UV-light to disrupt the C-S bond allows for the formation of thianthrene radical cations and aryl radicals.

ORGANIC LETTERS (2021)

Article Multidisciplinary Sciences

Generation of non-stabilized alkyl radicals from thianthrenium salts for C-B and C-C bond formation

Cheng Chen et al.

Summary: The authors present a method for generating non-stabilized alkyl radicals as key intermediates from S-(alkyl) thianthrenium salts, allowing for controlled and selective reactions under mild photoredox conditions. This approach has been shown to successfully construct alkylboronates and other important compounds, demonstrating its practicality and versatility in organic synthesis.

NATURE COMMUNICATIONS (2021)

Review Multidisciplinary Sciences

Recent advances in organic electrosynthesis employing transition metal complexes as electrocatalysts

Cong Ma et al.

Summary: Organic electrosynthesis utilizes electric current as a traceless redox agent, providing an environmentally conscious alternative; indirect electrolysis with redox catalysts can avoid overpotential of electron transfer, achieving wide functional group tolerance and selectivity control.

SCIENCE BULLETIN (2021)

Article Chemistry, Organic

Electrochemical oxygenation of sulfides with molecular oxygen or water: switchable preparation of sulfoxides and sulfones

Qi Xue et al.

Summary: This practical and eco-friendly method allows controllable aerobic oxygenation of sulfides by electrochemical catalysis. The switchable preparation of sulfoxides and sulfones is effectively controlled by reaction time, utilizing both molecular oxygen and water as the oxygen source under catalyst and external oxidant-free conditions. The electrochemical protocol features a broad substrate scope, excellent site selectivity, and successful application in modifying sulfide-containing pharmaceuticals and their derivatives.

ORGANIC & BIOMOLECULAR CHEMISTRY (2021)

Article Chemistry, Multidisciplinary

Photoredox catalysis with aryl sulfonium salts enables site-selective late-stage fluorination

Jiakun Li et al.

NATURE CHEMISTRY (2020)

Article Chemistry, Multidisciplinary

Para-selective borylation of monosubstituted benzenes using a transient mediator

Jie Wu et al.

SCIENCE CHINA-CHEMISTRY (2020)

Review Chemistry, Multidisciplinary

Catalyzing Electrosynthesis: A Homogeneous Electrocatalytic Approach to Reaction Discovery

Juno C. Siu et al.

ACCOUNTS OF CHEMICAL RESEARCH (2020)

Article Chemistry, Multidisciplinary

Arenesulfonyl Fluoride Synthesis via Copper-free Sandmeyer-type Fluorosulfonylation of Arenediazonium Salts

Qiongzhen Lin et al.

CHINESE JOURNAL OF CHEMISTRY (2020)

Article Chemistry, Multidisciplinary

Pd-Catalyzed Site-SelectiveBorylation of Simple Arenes via Thianthrenation

Xiao-Yue Chen et al.

CHINESE JOURNAL OF CHEMISTRY (2020)

Article Chemistry, Organic

Copper-free Sandmeyer-type Reaction for the Synthesis of Sulfonyl Fluorides

Tao Zhong et al.

ORGANIC LETTERS (2020)

Article Chemistry, Organic

Clickable Transformation of Nitriles (RCN) to Oxazolyl Sulfonyl Fluoride Warheads

Wan-Yin Fang et al.

ORGANIC LETTERS (2020)

Article Multidisciplinary Sciences

Site-selective and versatile aromatic C-H functionalization by thianthrenation

Florian Berger et al.

NATURE (2019)

Article Chemistry, Multidisciplinary

Sulfonyl Fluoride Synthesis through Electrochemical Oxidative Coupling of Thiols and Potassium Fluoride

Gabriele Laudadio et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2019)

Review Chemistry, Multidisciplinary

Chemistry with Electrochemically Generated N-Centered Radicals

Peng Xiong et al.

ACCOUNTS OF CHEMICAL RESEARCH (2019)

Article Chemistry, Multidisciplinary

Cyclic Alkenylsulfonyl Fluorides: Palladium-Catalyzed Synthesis and Functionalization of Compact Multifunctional Reagents

Terry Shing-Bong Lou et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019)

Review Chemistry, Organic

Applications of sulfuryl fluoride (SO2F2) in chemical transformations

Ravindar Lekkala et al.

ORGANIC CHEMISTRY FRONTIERS (2019)

Review Chemistry, Multidisciplinary

The growing applications of SuFEx click chemistry

A. S. Barrow et al.

CHEMICAL SOCIETY REVIEWS (2019)

Article Chemistry, Multidisciplinary

Electrochemical synthesis of enaminones via a decarboxylative coupling reaction

Xianqiang Kong et al.

GREEN CHEMISTRY (2019)

Editorial Material Chemistry, Medicinal

Emerging Utility of Fluorosulfate Chemical Probes

Lyn H. Jones

ACS MEDICINAL CHEMISTRY LETTERS (2018)

Review Chemistry, Organic

Insertion of sulfur dioxide via a radical process: an efficient route to sulfonyl compounds

Guanyinsheng Qiu et al.

ORGANIC CHEMISTRY FRONTIERS (2018)

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)

Article Chemistry, Multidisciplinary

SO2F2-Mediated Oxidative Dehydrogenation and Dehydration of Alcohols to Alkynes

Gao-Feng Zha et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2018)

Article Chemistry, Organic

Pd-Catalyzed Conversion of Aryl Iodides to Sulfonyl Fluorides Using SO2 Surrogate DABSO and Selectfluor

Ariana L. Tribby et al.

JOURNAL OF ORGANIC CHEMISTRY (2017)

Article Chemistry, Multidisciplinary

Copper(I)-catalyzed sulfonylative Suzuki-Miyaura cross-coupling

Yiding Chen et al.

CHEMICAL SCIENCE (2017)

Review Chemistry, Multidisciplinary

Synthetic Organic Electrochemical Methods Since 2000: On the Verge of a Renaissance

Ming Yan et al.

CHEMICAL REVIEWS (2017)

Article Chemistry, Multidisciplinary

Catalyst-free radical fluorination of sulfonyl hydrazides in water

Lin Tang et al.

GREEN CHEMISTRY (2016)

Article Chemistry, Multidisciplinary

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

Matthew K. Nielsen et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2015)

Review Chemistry, Multidisciplinary

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

Jiajia Dong et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2014)