Abstract
AbstractWhile the electrooxidative activation of carboxylic acids is an attractive synthetic methodology, the resulting transformations are generally limited to either homocoupling or further oxidation followed by solvent capture. These reactions require extensive electrolysis at high potentials, which ultimately renders the methodology incompatible with metal catalysts that could possibly provide new and complementary product distributions. This work establishes a proof-of-concept for a rare and synthetically-underutilized strategy for selective electrooxidation of carboxylic acids in the presence of oxidatively-sensitive catalysts that control reaction selectivity. We leverage the formation of self-adsorbed monolayers of carboxylate substrates at the anode to promote selective oxidation of the adsorbed carboxylate over a more easily-oxidized catalyst. Consequently, reactions operate at lower potentials, greater faradaic efficiencies, and improved catalyst compatibility over conventional approaches, which enables reactions to be performed with inexpensive Fe complexes that catalyze selective radical additions to olefins.
Funder
U.S. Department of Health & Human Services | NIH | National Institute of General Medical Sciences
Publisher
Springer Science and Business Media LLC
Subject
General Physics and Astronomy,General Biochemistry, Genetics and Molecular Biology,General Chemistry,Multidisciplinary
Cited by
18 articles.
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