Cu-Catalyzed Generation of Alkyl Radicals from Alkylsilyl Peroxides and Subsequent C(sp³)-C(sp²) Cross-Coupling with Arylboronic Acids

Shunya Sakurai, Saori Tsuzuki, Ryu Sakamoto and Keiji Maruoka*

*Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto 606-8502, Japan, Email: maruoka.keiji.4wkyoto-u.ac.jp

S. Sakurai, S. Tsuzuki, R. Sakamoto, K. Maruoka, J. Org. Chem., 2020, 85, 3973-3980.

DOI: 10.1021/acs.joc.9b03294

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Abstract

A practical Cu-catalyzed C(sp³)-C(sp²) cross-coupling of alkylsilyl peroxides with arylboronic acids provides alkyl-substituted aromatic rings smoothly at room temperature. The reductive cleavage of the O-O bond and the desired cross-coupling reactions are promoted by simple Cu-based catalysts and do not require activation by visible light.

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Key Words

alkylation, ketones

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ID: J42-Y2020