Journal ArticleConversion of esters to thioesters under mild conditionsShi, Yijun; Liu, Xuejing; Cao, Han; Bie, Fusheng; Han, Ying; Yan, Peng; Szostak, Roman; Szostak, Michal; Liu, ChengweinullWe report conversion of esters to thioesters via selective C–O bond cleavage/weak C–S bond formation under transition-metal-free conditions. The method is notable for a general and practical transition-metal-free system, broad substrate scope and excellent functional group tolerance. The strategy was successfully deployed in late-stage thioesterification, site-selective cross-coupling/thioesterification/decarbonylation and easy-to-handle gram scale thioesterification. Selectivity and computational studies were performed to gain insight into the formation of weak C–S bonds by C–O bond cleavage, which contrasts with the traditional trend of nucleophilic additions to carboxylic acid derivatives.2021-04-0810224919Organic & Biomolecular Chemistry19132991 to 29961477-0520https://doi.org/10.1039/D1OB00187F1650766National Science Foundation