Enantioselective Palladium-Catalyzed Hydrofluorination of Alkenylarenes

作者：Xuemei Yin, Bin Chen, Feng Qiu, Xihong Wang, Yang Liao, Min Wang, Xinxiang Lei, Jian Liao · 发表于：ACS Catalysis · 年份：2020 · DOI：10.1021/acscatal.9b05264 · 被引用次数：35 · 研究领域：Fluorine in Organic Chemistry、Catalytic C–H Functionalization Methods、Asymmetric Synthesis and Catalysis

Hydrofluorination of simple alkenes is an attractive strategy to prepare fluorine-containing molecules. However, the catalytic asymmetric hydrofluorination remains an ongoing challenge. Here, we describe a palladium(II)-catalyzed enantioselective hydrofluorination of alkenylarenes, by employing sulfoxide phosphine (SOP) as a chiral ligand, triarylphosphine as a secondary ligand, Selectfluor as a fluorine source, and trihexylsilane as a hydride source. Under the optimal reaction conditions, a range of chiral benzyl fluorides bearing different functional groups are obtained in good yields (up to 80%) with high enantiopurity (having an enantiomeric ratio of up to 94:6). Some mechanistic insight of this reaction is obtained using in situ one- and two-dimensional 1 H– 31 P HMBC nuclear magnetic resonance spectroscopy and a catalytic cycle is proposed.