Sulfoxide-mediated oxidative cross-coupling of phenols
Sulfoxide-mediated oxidative cross-coupling of phenols
A metal-free, oxidative coupling of phenols with various nucleophiles, including arenes, 1,3-diketones and other phenols, is reported. Cross-coupling is mediated by a sulfoxide which inverts the reactivity of the phenol partner. Crucially, the process shows high selectivity for cross-versus homo-coupling and allows efficient access to a variety of aromatic scaffolds including biaryls, benzofurans and, through an iterative procedure, aromatic oligomers.
2001-2005
He, Zhen
867c52b8-34d4-46b2-a59f-0b6801f827d2
Perry, Gregory J.P.
766e7fc8-abf3-4d1e-9949-c1b3439a2185
Procter, David J.
7642b405-d26f-4064-b0d2-8a1d562348b4
He, Zhen
867c52b8-34d4-46b2-a59f-0b6801f827d2
Perry, Gregory J.P.
766e7fc8-abf3-4d1e-9949-c1b3439a2185
Procter, David J.
7642b405-d26f-4064-b0d2-8a1d562348b4
He, Zhen, Perry, Gregory J.P. and Procter, David J.
(2020)
Sulfoxide-mediated oxidative cross-coupling of phenols.
Chemical Science, 11 (7), .
(doi:10.1039/c9sc05668h).
Abstract
A metal-free, oxidative coupling of phenols with various nucleophiles, including arenes, 1,3-diketones and other phenols, is reported. Cross-coupling is mediated by a sulfoxide which inverts the reactivity of the phenol partner. Crucially, the process shows high selectivity for cross-versus homo-coupling and allows efficient access to a variety of aromatic scaffolds including biaryls, benzofurans and, through an iterative procedure, aromatic oligomers.
Text
c9sc05668h
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More information
Accepted/In Press date: 9 January 2020
e-pub ahead of print date: 15 January 2020
Additional Information:
Funding Information:
We thank EPSRC (EP/M005062/1; Postdoctoral Fellowship to Z. H.; Established Career Fellowship to D. J. P.) and The University of Manchester (Lectureship to G. J. P.$P.) for their generous support.
Identifiers
Local EPrints ID: 478057
URI: http://eprints.soton.ac.uk/id/eprint/478057
ISSN: 2041-6520
PURE UUID: d1c61f6a-850c-464e-9f4f-403406b3cf5b
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Date deposited: 21 Jun 2023 16:41
Last modified: 18 Mar 2024 04:11
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Author:
Zhen He
Author:
Gregory J.P. Perry
Author:
David J. Procter
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