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Organocatalyzed Anodic Oxidation of Aldehydes to Thioesters

Kelli A. Ogawa and Andrew J. Boydston*

*Department of Chemistry, University of Washington, Seattle, Washington 98195, United States, Email: boydstonchem.washington.edu

K. A. Ogawa, A. J. Boydston, Org. Lett., 2014, 16, 1928-1931.

DOI: 10.1021/ol500459x (free Supporting Information)


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Abstract

A thiazolium precatalyst facilitates electrochemical oxidation of thiolate anions, leading to deleterious formation of disulfide byproducts. For the reaction of a broad range of aldehyde and thiol substrates, thioesters were obtained in very good yields . This approach provides an atom-efficient thioesterification that circumvents the need for stoichiometric exogenous oxidants, high cell potentials, or redox mediators.

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Key Words

thioesters, electrochemistry


ID: J54-Y2014