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 methods 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.