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Issue 9, 2017
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Photocatalytic esterification under Mitsunobu reaction conditions mediated by flavin and visible light

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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.

Graphical abstract: Photocatalytic esterification under Mitsunobu reaction conditions mediated by flavin and visible light

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Publication details

The article was received on 19 Dec 2016, accepted on 03 Feb 2017 and first published on 03 Feb 2017


Article type: Communication
DOI: 10.1039/C6OB02770A
Citation: Org. Biomol. Chem., 2017,15, 1970-1975
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    Photocatalytic esterification under Mitsunobu reaction conditions mediated by flavin and visible light

    M. März, J. Chudoba, M. Kohout and R. Cibulka, Org. Biomol. Chem., 2017, 15, 1970
    DOI: 10.1039/C6OB02770A

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