Deoxygenative Functionalization of Alcohols and Carbonyl Compounds via Electrochemical Reduction

Oxygen-containing functional groups are prevalent motifs in natural products and feedstock chemicals, but direct meth-ods for their deoxygenative transformation remain rare due to the difficult cleavage of the strong C–O bond. Here, we develop a general activation strategy that employs hydrosilanes as activating reagents for alcohols, carbonyls, and esters to afford a common silyl ether intermediate. Electrochemical reduction of the in-situ generated silyl ether results in C–O cleavage to afford a carbanion, which reacts with a number of electrophiles for the construction of C–Si, C–B, C–Ge, and C–Sn bonds.