The electrosynthesis of highly encumbered biaryls from aryl o-iodobenzyl ethers by a radical to polar crossover sequence
The electrosynthesis of highly encumbered biaryls from aryl o-iodobenzyl ethers by a radical to polar crossover sequence
Highly encumbered 2,2′,6-tri- and 2,2′,6,6′-tetra-substituted biaryls are readily prepared from aryl ortho-iodobenzyl ethers through mediated cathodic reduction under flow. The reaction proceeds via the stepwise transfer of two electrons: the first to induce loss of iodide and a radical cyclisation, and the second to induce a polar fragmentation.
4042-4045
Pearce, James E.
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Hodgson, Jack William
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Folgueiras amador, Ana A.
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Fish, Johanna A.
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Carroll, Robert C.
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Coles, Simon J.
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Parsons, Philip J.
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Brown, Richard C.D.
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Harrowven, David C.
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31 January 2025
Pearce, James E.
c8389bad-182d-4ac6-8af0-52fb40b9bb95
Hodgson, Jack William
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Folgueiras amador, Ana A.
080c345d-0a05-406a-bf7c-1939ca9c0aaa
Fish, Johanna A.
9de5c823-c554-415a-b4d5-431c31fb3679
Carroll, Robert C.
94d92c13-aec3-4d94-a7d4-7a4477b1eb64
Coles, Simon J.
3116f58b-c30c-48cf-bdd5-397d1c1fecf8
Parsons, Philip J.
94e68ded-a07b-4339-bf80-3f25c3347799
Brown, Richard C.D.
21ce697a-7c3a-480e-919f-429a3d8550f5
Harrowven, David C.
bddcfab6-dbde-49df-aec2-42abbcf5d10b
Pearce, James E., Hodgson, Jack William, Folgueiras amador, Ana A., Fish, Johanna A., Carroll, Robert C., Coles, Simon J., Parsons, Philip J., Brown, Richard C.D. and Harrowven, David C.
(2025)
The electrosynthesis of highly encumbered biaryls from aryl o-iodobenzyl ethers by a radical to polar crossover sequence.
Chemical Communications, 61 (20), .
(doi:10.1039/D4CC06061J).
Abstract
Highly encumbered 2,2′,6-tri- and 2,2′,6,6′-tetra-substituted biaryls are readily prepared from aryl ortho-iodobenzyl ethers through mediated cathodic reduction under flow. The reaction proceeds via the stepwise transfer of two electrons: the first to induce loss of iodide and a radical cyclisation, and the second to induce a polar fragmentation.
Text
d4cc06061j
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Accepted/In Press date: 28 January 2025
Published date: 31 January 2025
Identifiers
Local EPrints ID: 499301
URI: http://eprints.soton.ac.uk/id/eprint/499301
ISSN: 1359-7345
PURE UUID: 2af891f1-2323-41a6-8aa3-f929012003ef
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Date deposited: 14 Mar 2025 17:39
Last modified: 22 Aug 2025 01:44
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Author:
James E. Pearce
Author:
Jack William Hodgson
Author:
Ana A. Folgueiras amador
Author:
Robert C. Carroll
Author:
Philip J. Parsons
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