Direct Deoxygenation of α-Hydroxy and α,β-Dihydroxy Ketones Using a Silyl Lithium Reagent

A reliable method for the one-step direct deoxygenation of alpha-hydroxy ketones has been developed using a silyl lithium reagent and acetic anhydride. The method is metal-catalyst-free and does not require prefunctionalization of the hydroxy group prior to its removal. Deoxygenation of different primary, secondary, and tertiary alcohols was carried out with up to 98% isolated yield. Additionally, double deoxygenation was achieved when the present method was applied to alpha,beta-dihydroxy ketones to access the corresponding enones in a single step.

Automated summary

A reliable one-step method for the direct deoxygenation of α-hydroxy ketones has been developed using a silyl lithium reagent and acetic anhydride. The method is metal-catalyst-free and does not require prefunctionalization of the hydroxy group. The deoxygenation of different types of alcohols achieved high yields up to 98%. Additionally, double deoxygenation of α,β-dihydroxy ketones to produce enones in a single step was also demonstrated.