Visible-Light-Photoexcited Palladium-Catalyzed Silylmethylation of Benzyl Alcohol Derivatives

Haruki Mizoguchi*,Ryuji Yoshida, Haruka Ikeda, Akira Sakakura*
Synlett 2023, eFirst (Special Issue Dedicated to Prof. Hisashi Yamamoto)
DOI: 10.1055/s-0042-1752736

An intramolecular C–H silylmethylation of benzylic alcohol derivatives catalyzed by a visible-light-photoexcited palladium complex was developed. Irradiation of the palladium complex with blue LEDs resulted in efficient activation of a C–I bond, and subsequent intramolecular radical arylation afforded siloxacycle products. Selective protonation or oxidation of the C–Si bond of the cyclized materials afforded ortho-methylated and ortho-hydroxymethylated derivatives of the benzylic alcohol derivatives.