Visible-Light-Induced Nickel-Catalyzed Radical Cross-Couplings to Access α-Aryl-α-trifluoromethyl Alcohols

Feng Chen; Xiu-Hua Xu; Lingling Chu; Feng-Ling Qing

doi:10.1021/acs.orglett.2c03943

Visible-Light-Induced Nickel-Catalyzed Radical Cross-Couplings to Access α-Aryl-α-trifluoromethyl Alcohols

Org Lett. 2022 Dec 23;24(50):9332-9336. doi: 10.1021/acs.orglett.2c03943. Epub 2022 Dec 9.

Authors

Feng Chen¹, Xiu-Hua Xu¹, Lingling Chu², Feng-Ling Qing¹

Affiliations

¹ Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032, China.
² College of Chemistry and Chemical Engineering, Donghua University, 2999 North Renmin Lu, Shanghai 201620, China.

PMID: 36484514
DOI: 10.1021/acs.orglett.2c03943

Abstract

A photochemically induced nickel-catalyzed radical cross-coupling of phthalimido trifluoroethanol with aryl bromides to furnish α-aryl-α-trifluoromethyl alcohols is reported. This reaction proceeds via a photoinduced charge transfer of an electron donor-acceptor complex between Hantzsch ester and phthalimido trifluoroethanol, followed by 1,2-hydrogen atom transfer, to generate the α-hydroxytrifluoroethyl radical for the cross-coupling of aryl bromides. No exogenous photocatalysts or stoichiometric metal reductants are required in this mild and operationally simple protocol. Broad substrate compatibility and excellent functional group tolerance are observed.