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N-Heterocyclic Carbene-Mediated Oxidative Electrosynthesis of Esters in a Microflow Cell

Robert A. Green, Derek Pletcher, Stuart G. Leach and Richard C. D. Brown*

*Department of Chemistry, University of Illinois at Urbana-Champaign, 600 South Mathews Avenue, Urbana, Illinois 61801, United States, Email:

R. A. Green, D. Pletcher, S. G. Leach, R. C. D. Brown, Org. Lett., 2015, 17, 3290-3293.

DOI: 10.1021/acs.orglett.5b01459 (free Supporting Information)

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An efficient N-heterocyclic carbene (NHC)-mediated oxidative esterification of aldehydes in an undivided microfluidic electrolysis cell provides up to 4.3 g h-1 of product in a single pass with excellent yields at ambient temperature. The oxidative acylation reactions proceed with a 1:1 stoichiometry of aldehyde and alcohol (for primary alcohols) with remarkably short residence times in the electrolysis cell (<13 s) without electrolyte.

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Key Words

oxidative esterification, electrochemistry, flow chemistry

ID: J54-Y2015