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Diverse Synthesis of Chiral Trifluoromethylated Alkanes via Nickel-Catalyzed Enantioconvergent Reductive Hydroalkylation of Unactivated Olefins

Wenqing Guo, Cheng Li, Guobin Ma, Weiqi Tong, Fan Wu

2022Organic Letters28 citationsDOI

Abstract

Here, we report a nickel-catalyzed enantioconvergent hydroalkylation of olefins with trifluoromethyl-containing α-alkyl halides for the synthesis of enantioenriched trifluoromethylated alkanes. This reaction employs readily available and bench-stable alkenes as alkyl coupling partners, featuring mild conditions, a broad substrate scope, and high functional group tolerance. The synthetic utility of this method is further demonstrated in the late-stage functionalization of a range of drug molecules and natural products.

Topics & Concepts

ChemistryCatalysisAlkylOrganic chemistryTrifluoromethylSubstrate (aquarium)HalideNickelCombinatorial chemistryEnantioselective synthesisGeologyOceanographyFluorine in Organic ChemistryCatalytic C–H Functionalization MethodsRadical Photochemical Reactions
Diverse Synthesis of Chiral Trifluoromethylated Alkanes via Nickel-Catalyzed Enantioconvergent Reductive Hydroalkylation of Unactivated Olefins | Litcius