Open AccessDecarbonylative sulfide synthesis from carboxylic acids and thioesters via cross-over C–S activation and acyl capture
Author(s) -
Chengwei Liu,
Michal Szostak
Publication year - 2021
Publication title -
organic chemistry frontiers
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.377
H-Index - 56
eISSN - 2052-4129
pISSN - 2052-4110
DOI - 10.1039/d1qo00824b
Subject(s) - chemistry , electrophile , thioester , nucleophile , carboxylic acid , aryl , combinatorial chemistry , reagent , sulfide , organic chemistry , derivatization , sulfur , catalysis , alkyl , high performance liquid chromatography , enzyme
A method for the synthesis of sulfides from carboxylic acids via thioester C-S activation and acyl capture has been accomplished, wherein thioesters serve as dual electrophilic activators to carboxylic acids as well as S-nucleophiles through the merger of decarbonylative palladium catalysis and sulfur coupling. This new concept engages readily available carboxylic acids as coupling partners to directly intercept sulfur reagents via redox-neutral thioester-enabled cross-over thioetherification. The scope of this platform is demonstrated in the highly selective decarbonylative thioetherification of a variety of carboxylic acids and thioesters, including late-stage derivatization of pharmaceuticals and natural products. This method operates under mild, external base-free, operationally-practical conditions, providing a powerful new framework to unlock aryl electrophiles from carboxylic acids and bolster the reactivity by employing common building blocks in organic synthesis.