Work

Deoxygenative Functionalization of Alcohols and Carbonyl Compounds via Electrochemical Reduction

Year: 2025

Type: article

Abstract: 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.

Source: Angewandte Chemie

DOI: 10.1002/ange.202510069

Authors: Andrew J. Ressler, Jesus I. Martinez Alvarado, Ruchira Hariharan, Weiyang Guan, Song Lin

Institution: Cornell University

Language: English

Topic: Radical Photochemical Reactions

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funders: National Science Foundation, Division of Chemistry

Awards: G1134277896, MRI: Acquisition of a Cryogenic Probe and Modern Console for Outstanding NMR Sensitivity to Benefit Research and Education at Cornell University, G8389919011