Electrochemical Conversion of N‐Sulfinylamines to Sulfonimidoyl Fluorides DOI Open Access

Fang‐Ling Gao,

Xinglei He,

Bin Zhao

et al.

Chinese Journal of Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 26, 2024

Comprehensive Summary The invention of novel linkers is a long‐lasting task in the area sulfur(VI) fluoride exchange reaction (SuFEx). Compared with most frequently investigated sulfonyl fluorides, synthetic accessibility toward its mono‐aza isostere, i.e. , sulfonimidoyl fluorides still limited. Herein, we report an electrochemical carbonfluorination readily available N ‐sulfinylamines to access various aryl and alkyl fluorides. transformation characterized by ready availability starting materials, mild conditions, obviating metal catalysts chemical oxidants.

Language: Английский

A Practical Electrochemical Approach for Synthesizing Selenyl-Dihydrobenzofurans and Chromane with a Tetrasubstituted Carbon Center DOI
Xianqiang Kong, Xiaohong Chen, Zhong‐Yan Cao

et al.

Synthesis, Journal Year: 2024, Volume and Issue: 56(17), P. 2695 - 2702

Published: June 24, 2024

Abstract A straightforward and efficient electrochemical method for the anodic oxidative selenenylation of 2-(2-arylallyl)phenols a 2-(3-arylbut-3-en-1-yl)phenol with diselenides under ambient air conditions has been outlined. This allows synthesis selenyl-dihydrobenzofurans chromane featuring sterically hindered tetrasubstituted carbon center, demonstrated through 25 examples yields reaching up to 98%. Initial mechanistic investigations suggest likely participation pivotal seleniranium cation species in regulating reactivity.

Language: Английский

Citations

2

Recent progress in sulfonyl fluoride synthesis via the radical sulfur dioxide insertion and fluorination strategy DOI

Haozhen Zhang,

Wangchuan Xiao,

Fanhong Wu

et al.

Science China Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 8, 2024

Language: Английский

Citations

2

Electroreduction Reactions Mediated by Organic Molecules: Recent Advances and Applications DOI Open Access
Yubing Huang

European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 27(47)

Published: Aug. 27, 2024

Abstract Electroreduction is an important aspect of organic electrochemistry. Its chemistry does not require the addition additional reductants, making it effective alternative to various traditional reduction reactions. Among them, organo‐mediated electroreduction recognized as a promising approach. Organo‐mediators can be reduced directly at cathode form reactive radical anions that subsequently reduce substrate via electron transfer ( ET ) initiate reaction being investigated. typically have more positive potential, and their role in whole similar catalysts. Their transforms process from original heterogeneous into homogeneous one. Organo‐mediated effectively avoid over‐electrolysis product electrode intolerance sensitive substrates or functional groups during electrolysis, thereby preventing occurrence side It also prevent excessive consumption reagents electrical energy while promoting achieve higher completely different selectivity. Considering advantages this type reaction, review will provide detailed description reactions mediated by molecules recent years elucidate mechanism organo‐mediators transformations.

Language: Английский

Citations

1

Electrochemically Driven Denitrative Cyanation of Nitroarenes DOI
Yiyi Chen,

Qisheng Chen,

Shuangquan Zhang

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(36), P. 7555 - 7559

Published: Sept. 3, 2024

A practical denitrative cyanation of feedstock nitroarenes under mild and transition metal-free reaction conditions has been developed. The key to success lies in the use electrochemically driven, inexpensive ionic liquid

Language: Английский

Citations

1

Enantioselective Synthesis of Chiral Sulfonimidoyl Fluorides Facilitates Stereospecific SuFEx Click Chemistry DOI Open Access

He-sen Huang,

Yi Yuan, Wei Wang

et al.

Angewandte Chemie, Journal Year: 2024, Volume and Issue: unknown

Published: Nov. 5, 2024

Abstract Sulfur‐centered electrophilic ‘warheads’ have emerged as key components for chemical proteomic probes through sulfur‐exchange chemistry (SuFEx) with protein nucleophiles. Among these functional groups, sulfonimidoyl fluorides (SIFs) stand out their modifiable sites, tunable electrophilicities, and chiral sulfur‐center, presenting exciting possibilities new covalent probes. However, the synthetic access to SIFs has been a challenge, limiting exploration applications. In this study, we describe convenient route obtain from readily available sulfenamides via series of one‐pot tandem reactions high enantiomeric excess (ees). The resulting were further converted into diverse array S(VI) derivatives under mild conditions or in buffer solutions. Most significantly, specificity ligation experiments underscored critical role sulfur‐center chirality design screening more‐selective therapeutics.

Language: Английский

Citations

1

Nickel-Catalyzed Direct Fluorosulfonylation of Vinyl Bromides and Benzyl Bromides for Sulfonyl Fluorides DOI
Jianquan Hong, Xiaoyu Wang, Kui Zhao

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(46), P. 9967 - 9972

Published: Nov. 8, 2024

An efficient nickel-catalyzed direct fluorosulfonylation of vinyl bromides and benzyl under mild reaction conditions has been developed for sulfonyl fluorides utilizing Na

Language: Английский

Citations

1

Copper-mediated assembly of SO2F group via radical fluorine-atom transfer strategy DOI

Yu-Yu Tan,

Lin-Heng He,

Wei‐Min He

et al.

Chinese Chemical Letters, Journal Year: 2024, Volume and Issue: 35(9), P. 109986 - 109986

Published: May 10, 2024

Language: Английский

Citations

0

Electrochemical Conversion of N‐Sulfinylamines to Sulfonimidoyl Fluorides DOI Open Access

Fang‐Ling Gao,

Xinglei He,

Bin Zhao

et al.

Chinese Journal of Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 26, 2024

Comprehensive Summary The invention of novel linkers is a long‐lasting task in the area sulfur(VI) fluoride exchange reaction (SuFEx). Compared with most frequently investigated sulfonyl fluorides, synthetic accessibility toward its mono‐aza isostere, i.e. , sulfonimidoyl fluorides still limited. Herein, we report an electrochemical carbonfluorination readily available N ‐sulfinylamines to access various aryl and alkyl fluorides. transformation characterized by ready availability starting materials, mild conditions, obviating metal catalysts chemical oxidants.

Language: Английский

Citations

0