Electrochemical Reduction of C-O Bonds

Abstract

Reductive activation and transformation of C-O bonds in alcohols have been a challenge for many decades, yet is still considered an important step in the process of converting biomass into biofuel and chemicals. The challenge arises from the cleavage of the carbon-oxygen bond which generally requires forcing conditions and is reflected in the high bond dissociation energy compared to other polarised sigma bonds.[1] Our project focuses on electroreductive cleavage of alcohols in the presence of a hydrogen donor in an undivided cell with up to 95% of the corresponding alkane. C-O transformation is also accomplished through carboxylation with carbon dioxide, resulting in yield up to 43%.[2][1] Villo, P.; Shatskiy, A.; Kärkäs, M. D.; Lundberg, H. Electrosynthetic C−O Bond Activation in Alcohols and Alcohol Derivatives. Angewandte Chemie International Edition 2023, 62 (4), e202211952. https://doi.org/10.1002/anie.202211952.[2] Villo, P.; Lill, M.; Alsaman, Z.; Kronberg, A. S.; Chu, V.; Ahumada, G.; Agarwala, H.; Ahlquist, M.; Lundberg, H. Electroreductive Deoxygenative C–H and C–C Bond Formation from Non-Derivatized Alcohols Fueled by Borohydride Oxidation. ChemRxiv August 2, 2023. https://doi.org/10.26434/chemrxiv-2023-tw9l1-v2. Figure 1