Organo-Photoredox Catalyzed <i>gem</i>-Difluoroallylation of Glycine and Glycine Residue in Peptides
Ruofan Lin, Yujie Shan, Yan Li, Xian Wei, Yue Zhang, Yuqian Lin, Yiman Gao, Weiwei Fang, Jing‐Jing Zhang, Ting Wu, Lingchao Cai, Zhen Chen
Abstract
An organo-photoredox catalyzed gem -difluoroallylation of glycine with α-trifluoromethyl alkenes via direct C(sp 3 )–H functionalization of glycine and C–F bond activation of α-trifluoromethyl alkenes has been described. As a consequence, a broad range of gem -difluoroalkene-containing unnatural amino acids are afforded in moderate to excellent yields. This reaction exhibits multiple merits such as readily available starting materials, broad substrate scope, and mild reaction conditions. The feasibility of this reaction has been highlighted by the late-stage modification of several peptides as well as the improved in vitro antifungal activity of compound 3v toward Valsa mali compared to that with commercial azoxystrobin.