Palladium-Catalyzed Benzylic Silylation of Diarylmethyl Carbonates with Silylboranes under Base-Free Conditions

A palladium-catalyzed benzylic silylation of diarylmethyl carbonates with silylboranes has been developed. The reaction proceeds smoothly even under external base-free conditions, and the corresponding benzylic silanes are formed in good to high yields. The obtained benzyl silane derivatives can work as the benzylic nucleophiles by the action of a suitable fluoride source and react with some carbon electrophiles to deliver the corresponding benzylic C-C cross-coupled products. Additionally, while still preliminary, the allylic silylation of the isoelectronic allylic carbonates is also achieved.

Automated summary

A new method for the palladium-catalyzed benzylic silylation of diarylmethyl carbonates with silylboranes has been developed. The reaction proceeds smoothly even without external base, and high yields of benzylic silanes are obtained. The obtained silanes can work as nucleophiles and react with carbon electrophiles to deliver benzylic C-C cross-coupled products.