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Visible-Light-Promoted Hydroxydifluoroalkylation of Alkenes Enabled by Electron Donor–Acceptor Complex

Zhenzhen Xie, Yu Zheng, Kai Tang, Jianping Guan, Chu‐Ping Yuan, Jun‐An Xiao, Hao‐Yue Xiang, Kai Chen, Xiaoqing Chen, Hua Yang

2021Organic Letters43 citationsDOI

Abstract

A catalyst-free strategy for regioselective hydroxydifluoroalkylation of alkenes with alkyl bromides was developed, affording a series of difluoroalkylated tertiary alcohols in moderate to good yields. This photocatalyst-free protocol shows broad substrate scope under mild conditions. Moreover, mechanistic studies revealed that a newly identified electron donor-acceptor complex is crucial to this transformation.

Topics & Concepts

ChemistryRegioselectivityCatalysisElectron donorAcceptorElectron acceptorAlkylSubstrate (aquarium)PhotochemistryCombinatorial chemistryPhotocatalysisVisible spectrumOrganic chemistryPhysicsCondensed matter physicsOceanographyOptoelectronicsGeologyFluorine in Organic ChemistryRadical Photochemical ReactionsCatalytic C–H Functionalization Methods
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