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Visible-Light-Induced Nickel-Catalyzed Radical Cross-Couplings to Access α-Aryl-α-trifluoromethyl Alcohols
Feng Chen1, Xiu-Hua Xu1, Lingling Chu2
1Key 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.
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.
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