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N-heterocyclic carbene-mediated oxidative electrosynthesis of esters in a microflow cell

N-heterocyclic carbene-mediated oxidative electrosynthesis of esters in a microflow cell
N-heterocyclic carbene-mediated oxidative electrosynthesis of esters in a microflow cell
An efficient N-heterocyclic carbene (NHC)-mediated oxidative esterification of aldehydes has been achieved in an undivided microfluidic electrolysis cell at ambient temperature. Productivities of up to 4.3 g h?1 in a single pass are demonstrated, with excellent yields and conversions for 19 examples presented. Notably, the oxidative acylation reactions were shown to proceed with a 1:1 stoichiometry of aldehyde and alcohol (for primary alcohols), with remarkably short residence times in the electrolysis cell (<13 s), and without added electrolyte.
1523-7060
3920-3293
Green, Robert Aaron
f18e5445-0d58-4adf-8874-2bb3b6ecc402
Brown, Richard C. D.
21ce697a-7c3a-480e-919f-429a3d8550f5
Pletcher, Derek
f22ebe69-b859-4a89-80b0-9e190e6f8f30
Leach, Stuart
80f0a3ee-1890-4f47-9b78-3f407ce2907c
Green, Robert Aaron
f18e5445-0d58-4adf-8874-2bb3b6ecc402
Brown, Richard C. D.
21ce697a-7c3a-480e-919f-429a3d8550f5
Pletcher, Derek
f22ebe69-b859-4a89-80b0-9e190e6f8f30
Leach, Stuart
80f0a3ee-1890-4f47-9b78-3f407ce2907c

Green, Robert Aaron, Brown, Richard C. D., Pletcher, Derek and Leach, Stuart (2015) N-heterocyclic carbene-mediated oxidative electrosynthesis of esters in a microflow cell. Organic Letters, 17 (13), 3920-3293. (doi:10.1021/acs.orglett.5b01459).

Record type: Article

Abstract

An efficient N-heterocyclic carbene (NHC)-mediated oxidative esterification of aldehydes has been achieved in an undivided microfluidic electrolysis cell at ambient temperature. Productivities of up to 4.3 g h?1 in a single pass are demonstrated, with excellent yields and conversions for 19 examples presented. Notably, the oxidative acylation reactions were shown to proceed with a 1:1 stoichiometry of aldehyde and alcohol (for primary alcohols), with remarkably short residence times in the electrolysis cell (<13 s), and without added electrolyte.

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Accepted/In Press date: 8 June 2015
Published date: 15 June 2015
Organisations: Organic Chemistry: Synthesis, Catalysis and Flow

Identifiers

Local EPrints ID: 380329
URI: https://eprints.soton.ac.uk/id/eprint/380329
ISSN: 1523-7060
PURE UUID: 99076255-965c-4e89-9cbd-01fc3f42cdd1
ORCID for Richard C. D. Brown: ORCID iD orcid.org/0000-0003-0156-7087

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Date deposited: 08 Sep 2015 14:47
Last modified: 15 Aug 2019 00:52

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