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

This work describes a novel and practical method for the Cu-catalyzed C(sp(3))-C(sp(2)) 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(sp(3))-C(sp(2)) bond formation via beta-scission of the alkoxy radicals generated from the alkylsilyl peroxides.