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

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journal contribution
posted on 10.02.2020, 19:09 by Shunya Sakurai, Saori Tsuzuki, Ryu Sakamoto, Keiji Maruoka
This work describes a novel and practical method for the Cu-catalyzed C­(sp3)–C­(sp2) cross-coupling of alkylsilyl peroxides with arylboronic acids. The reductive cleavage of the O–O bond of alkylsilyl peroxides and the desired cross-coupling reactions to afford alkyl-substituted aromatic rings proceed smoothly at room temperature promoted by simple Cu-based catalysts and do not require activation by visible light. The results of mechanistic investigations support a radical-mediated C­(sp3)–C­(sp2) bond formation via β-scission of the alkoxy radicals generated from the alkylsilyl peroxides.