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Updated: Mar 7, 2026

Light-driven Enzymatic Decarboxylation
Published on: May 22, 2016
Photocatalytic esterification under Mitsunobu reaction conditions mediated by flavin and visible light
M März1, J Chudoba2, M Kohout1
1Department of Organic Chemistry, University of Chemistry and Technology, Prague, Technická 5, 166 28 Prague, Czech Republic. cibulkar@vscht.cz.
Abstract:
The usefulness of flavin-based aerial photooxidation in esterification under Mitsunobu reaction conditions was demonstrated, providing aerial dialkyl azodicarboxylate recycling/generation from the corresponding dialkyl hydrazine dicarboxylate. Simultaneously, activation of triphenylphosphine (Ph3P) by photoinduced electron transfer from flavin allows azo-reagent-free esterification. An optimized system with 3-methylriboflavin tetraacetate (10%), oxygen (terminal oxidant), visible light (450 nm), Ph3P, and dialkyl hydrazine dicarboxylate (10%) has been shown to provide efficient and stereoselective coupling of various alcohols and acids to esters with retention of configuration.
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