N-Heterocyclic Carbene-mediated microfluidic oxidative electrosynthesis of amides from aldehydes
N-Heterocyclic Carbene-mediated microfluidic oxidative electrosynthesis of amides from aldehydes
A flow process for N-Heterocyclic Carbene (NHC)-mediated anodic oxidative amidation of aldehydes is described, employing an undivided microfluidic electrolysis cell to oxidize Breslow intermediates. After electrochemical oxidation, the reaction of the intermediate N-acylated thiazolium cation with primary amines is completed by passage through a heating cell to achieve high conversion in a single pass. The flow mixing regimen circumvented the issue of competing imine formation between the aldehyde and amine substrates, which otherwise prevented formation of the desired product. High yields (71–99%), productivities (up to 2.6 g h–1), and current efficiencies (65–91%) were realized for 19 amides.
1198-1201
Green, Robert A.
dd77b072-3972-4b58-921c-cce36691592f
Pletcher, Derek
f22ebe69-b859-4a89-80b0-9e190e6f8f30
Leach, Stuart A.
6bf5fd7a-7d6f-431f-af65-41e0f98e8384
Brown, Richard C.D.
21ce697a-7c3a-480e-919f-429a3d8550f5
4 March 2016
Green, Robert A.
dd77b072-3972-4b58-921c-cce36691592f
Pletcher, Derek
f22ebe69-b859-4a89-80b0-9e190e6f8f30
Leach, Stuart A.
6bf5fd7a-7d6f-431f-af65-41e0f98e8384
Brown, Richard C.D.
21ce697a-7c3a-480e-919f-429a3d8550f5
Green, Robert A., Pletcher, Derek, Leach, Stuart A. and Brown, Richard C.D.
(2016)
N-Heterocyclic Carbene-mediated microfluidic oxidative electrosynthesis of amides from aldehydes.
Organic Letters, 18 (5), .
(doi:10.1021/acs.orglett.6b00339).
Abstract
A flow process for N-Heterocyclic Carbene (NHC)-mediated anodic oxidative amidation of aldehydes is described, employing an undivided microfluidic electrolysis cell to oxidize Breslow intermediates. After electrochemical oxidation, the reaction of the intermediate N-acylated thiazolium cation with primary amines is completed by passage through a heating cell to achieve high conversion in a single pass. The flow mixing regimen circumvented the issue of competing imine formation between the aldehyde and amine substrates, which otherwise prevented formation of the desired product. High yields (71–99%), productivities (up to 2.6 g h–1), and current efficiencies (65–91%) were realized for 19 amides.
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eprints version of amidation paper.pdf
- Accepted Manuscript
Text
acs%2Eorglett%2E6b00339.pdf
- Version of Record
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e-pub ahead of print date: 17 February 2016
Published date: 4 March 2016
Organisations:
Organic Chemistry: Synthesis, Catalysis and Flow
Identifiers
Local EPrints ID: 392630
URI: http://eprints.soton.ac.uk/id/eprint/392630
ISSN: 1523-7060
PURE UUID: 72e87e82-943f-4001-9004-60ecb60e9ccd
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Date deposited: 14 Apr 2016 11:04
Last modified: 15 Mar 2024 05:29
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Author:
Robert A. Green
Author:
Stuart A. Leach
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