2023/03/13 by Hengyuan Li, Chuanle Zhu · 2 citations
Pharmacology, Toxicology and Pharmaceutics · Chemical Engineering · Chemistry · #Fluorine in Organic Chemistry #Carbon dioxide utilization in catalysis #Inorganic Fluorides and Related Compounds
paper · doi:10.1021/acs.joc.2c02568
Purification-controlled defluorinative esterification and 1,3-dietherification of (trifluoromethyl)alkenes with alcohols are achieved, delivering various useful α-arylacrylates and 1,3-diethers in high yields. Remarkably, this reaction enables the cleavage of three C–F bonds in a CF 3 group, and it is transition-metal free and catalyst-free, has simple operation, features mild conditions, is gram-scalable, and has broad substrate scope and valuable functional group tolerance. Mechanism studies indicated that the isolated monofluoroalkene-decorated 1,3-diethers are the intermediates, and the acidic property of silica gel assisted the defluorinative transformation of these 1,3-diethers to access α-arylacrylates with H 2 O as the oxygen source.