617-02-7Relevant articles and documents
Conversion of esters to thioesters under mild conditions
Shi, Yijun,Liu, Xuejing,Cao, Han,Bie, Fusheng,Han, Ying,Yan, Peng,Szostak, Roman,Szostak, Michal,Liu, Chengwei
supporting information, p. 2991 - 2996 (2021/04/14)
We report conversion of esters to thioestersviaselective 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.
Unexpected migration of a benzoyl group in the intramolecular Wittig reaction of o-acyloxybenzylidenephosphoranes with benzoyl chlorides: One-pot synthesis of isomeric 3-benzoyl-2-phenylbenzofurans
Begala, Michela,Mancinelli, Michele,Delogu, Giovanna Lucia
supporting information, (2020/01/28)
The reaction of o-acyloxybenzylidenetriphenylphosphoranes with substituted benzoyl chlorides in an aprotic solvent led, together with the expected 2-phenylbenzofuran, to isomeric 3-benzoyl-2-phenylbenzofuran derivatives. This result formally corresponds to intramolecular migration of the benzoyl group from the ortho oxygen atom to the ylide carbanion via cyclization and ring opening of the starting o-acyloxybenzylidenetriphenylphosphoranes.
Visible light-mediated transition metal-free esterification of amides with boronic acids
Ding, Hao,Qi, Wan-Ying,Zhen, Jing-Song,Ding, Qiuping,Luo, Yong
supporting information, (2020/10/02)
A novel strategy for visible light-mediated esterification of amides with boronic acids in air has been described. This method is characterized by mild reaction conditions and low cost owing to no need of any catalyst, which implies high potential utility in late-stage functionalization of amide drugs and materials.