Trifluoromethylation of Carbonyl and Unactivated Olefin Derivatives by C(sp3 )-C Bond Cleavage

Fei Cong; Riccardo S Mega; Jinhong Chen; Craig S Day; Ruben Martin

doi:10.1002/anie.202214633

Trifluoromethylation of Carbonyl and Unactivated Olefin Derivatives by C(sp³ )-C Bond Cleavage

Angew Chem Int Ed Engl. 2023 Apr 3;62(15):e202214633. doi: 10.1002/anie.202214633. Epub 2022 Dec 12.

Authors

Fei Cong^{1

2}, Riccardo S Mega¹, Jinhong Chen^{1

2}, Craig S Day^{1

2}, Ruben Martin^{1

3}

Affiliations

¹ Institute of Chemical Research of Catalonia (ICIQ), The Barcelona Institute of Science and Technology, Av. Països Catalans 16, 43007, Tarragona, Spain.
² Departament de Química Analítica i Química Orgànica, Universitat Rovira i Virgili, c/Marcel ⋅ lí Domingo, 1, 43007, Tarragona, Spain.
³ Catalan Institution for Research and Advanced Studies (ICREA), Passeig Lluïs Companys 23, 08010, Barcelona, Spain.

PMID: 36416716
DOI: 10.1002/anie.202214633

Abstract

Herein, we report a Cu-mediated trifluoromethylation of carbonyl-type compounds and unactivated olefins enabled by visible-light irradiation via σ C(sp³ )-C bond-functionalization. The reaction is distinguished by its modularity, mild conditions and wide scope-even in the context of late-stage functionalization-thus offering a complementary approach en route to valuable C(sp³ )-CF₃ architectures from easily accessible precursors.

Keywords: Cross-Coupling; C−C Bond Cleavage; Pro-Aromatic Precursors; Radical Intermediates; Trifluoromethylation.

Abstract

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