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

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.

Automated summary

An intramolecular C-H silylmethylation of benzylic alcohol derivatives was achieved using a visible-light-photoexcited palladium complex as the catalyst. Blue LED irradiation activated a C-I bond, and subsequent intramolecular radical arylation led to the formation of 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.