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: rcb1
soton.ac.uk
R. A. Green, D. Pletcher, S. G. Leach, R. C. D. Brown, Org. Lett., 2015, 17, 3290-3293.
DOI: 10.1021/acs.orglett.5b01459
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Abstract
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
