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Copper Catalyzed C(sp3)-H Bond Alkylation via Photoinduced Ligand-to-Metal Charge Transfer

Sean M. Treacy and Tomislav Rovis*

*Department of Chemistry, Columbia University, New York, New York 10027, United States, Email:

S. M. Treacy, T. Rovis, J. Am. Chem. Soc., 2021, 143, 2729-2735.

DOI: 10.1021/jacs.1c00687

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CuCl2 catalyzes a coupling of unactivated C(sp3)-H bonds of numerous feedstock chemicals with electron-deficient olefins. The active cuprate catalyst undergoes Ligand-to-Metal Charge Transfer (LMCT) to enable the generation of a chlorine radical which acts as a powerful hydrogen atom transfer reagent capable of abstracting strong electron-rich C(sp3)-H bonds.

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proposed mechanism

Key Words

cyclopentanes, cyclohexanes, cycloheptanes, cyclooctanes, 1,4-addition

ID: J48-Y2021