Copper‐Mediated Decarboxylative Trifluoromethylselenolation of Alkynyl Carboxylic Acids with [Me4N][SeCF3] DOI Open Access
Xue Ding,

Yu‐Fei Yao,

Jiangyu Li

et al.

European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 30, 2024

Abstract The synthesis of alkynyl trifluoromethyl selenoethers from copper‐mediated aerobic decarboxylative trifluoromethylselenolation carboxylic acids with [Me 4 N][SeCF 3 ] is reported. reaction proceeded smoothly under mild conditions and enabled the facile conversion both aryl alkyl to corresponding in good yields, demonstrating that nucleophilic reagent feasible at ambient temperature without irradiation. Advantages method include use bench‐stable non‐volatile as starting materials, readily accessible SeCF reagent, excellent functional group tolerance, avoidance harsh conditions. This represents first a source.

Language: Английский

Photocatalytic Three-Component Reductive Coupling Synthesis of gem-Difluorohomoallyl Secondary Amines DOI

Bingbing Feng,

Meifang Tang,

Rui Xiao

et al.

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 23, 2025

gem-Difluorohomoallyl amines, an important class of gem-difluoroalkenes, are prevalent moieties in many bioactive compounds. However, limited methods suitable for the synthesis this type compound containing secondary amines. Here, we display a photocatalytic multicomponent protocol gem-difluoroalkenes which makes use readily available materials: arylamines, alkyl aldehydes, and α-trifluoromethyl alkenes. Moreover, ketones amines also substrates. Preliminary mechanistic experiments indicate that key α-amino radical was involved, generated from reduction situ-formed imines (or iminium ions) by reduced photocatalyst. Subsequent addition to alkenes β-F elimination deliver desired products.

Language: Английский

Citations

2
Progress in Photocatalyzed Trifluoromethylthiolation and Trifluoromethylselenolation Reactions DOI
Fei Li,

Jiawei Song,

Cheng‐Pan Zhang

et al.

Synthesis, Journal Year: 2024, Volume and Issue: unknown

Published: May 29, 2024

Abstract The trifluoromethylthio (SCF3) and trifluoromethylselanyl (SeCF3) groups possess high electron-withdrawing ability, excellent lipophilicity, good stability, bioavailability, they are promising structural motifs in drug design development. Photoredox catalysis has clear benefits; it is a mild sustainable methodology for the modification of chemical structures that enables variety reactions unattainable using classical ionic chemistry. This review focuses on light-initiated trifluoromethylthiolation trifluoromethylselenolation with diverse SCF3 SeCF3 reagents. Representative transformations either photocatalysts or through EDA complexes, as well possible reaction mechanisms, all discussed this article. 1 Introduction 2 Photocatalyzed Trifluoromethylthiolation 2.1 MSCF3 (M = H, [Me4N], Ag) 2.2 XSCF3 (X Cl, CF3S) 2.3 ArSO2SCF3 2.4 N–SCF3 Reagents 2.5 Other 3 Trifluoromethylselenolation 3.1 [Me4N][SeCF3] 3.2 ArSO2SeCF3 4 Summary

Language: Английский

Citations

2
Synthesis of Trifluoromethylselenolated Spiro[5.5]trienones/Spiro[4.5]trienones via Electrophilic Trifluoromethylselenolation Cyclization and Dearomatization DOI Open Access
Jia Wang, Jiaqi Niu,

Mingjiang Geng

et al.

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 15, 2024

Abstract An expedient strategy for the construction of trifluoromethylselenolated spiro[5.5]trienones/spiro[4.5]trienones through a cascade electrophilic trifluoromethylselenolation cyclization and dearomatization has been developed. This sequential process was induced by N ‐trifluoromethylselenophthalimide (Phth‐SeCF 3 ), which an efficient reagent. approach feature mild conditions, broad substrate scope, high functional group tolerance.

Language: Английский

Citations

0
Copper‐Mediated Decarboxylative Trifluoromethylselenolation of Alkynyl Carboxylic Acids with [Me4N][SeCF3] DOI Open Access
Xue Ding,

Yu‐Fei Yao,

Jiangyu Li

et al.

European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 30, 2024

Abstract The synthesis of alkynyl trifluoromethyl selenoethers from copper‐mediated aerobic decarboxylative trifluoromethylselenolation carboxylic acids with [Me 4 N][SeCF 3 ] is reported. reaction proceeded smoothly under mild conditions and enabled the facile conversion both aryl alkyl to corresponding in good yields, demonstrating that nucleophilic reagent feasible at ambient temperature without irradiation. Advantages method include use bench‐stable non‐volatile as starting materials, readily accessible SeCF reagent, excellent functional group tolerance, avoidance harsh conditions. This represents first a source.

Language: Английский

Citations

0