The University of Southampton
University of Southampton Institutional Repository

Sulfoxide-mediated oxidative cross-coupling of phenols

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.

2041-6520
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), 2001-2005. (doi:10.1039/c9sc05668h).

Record type: Article

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 - Version of Record
Available under License Creative Commons Attribution.
Download (1MB)

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
ORCID for Gregory J.P. Perry: ORCID iD orcid.org/0000-0001-8173-3369

Catalogue record

Date deposited: 21 Jun 2023 16:41
Last modified: 06 Jun 2024 02:17

Export record

Altmetrics

Contributors

Author: Zhen He
Author: Gregory J.P. Perry ORCID iD
Author: David J. Procter

Download statistics

Downloads from ePrints over the past year. Other digital versions may also be available to download e.g. from the publisher's website.

View more statistics

Atom RSS 1.0 RSS 2.0

Contact ePrints Soton: eprints@soton.ac.uk

ePrints Soton supports OAI 2.0 with a base URL of http://eprints.soton.ac.uk/cgi/oai2

This repository has been built using EPrints software, developed at the University of Southampton, but available to everyone to use.

We use cookies to ensure that we give you the best experience on our website. If you continue without changing your settings, we will assume that you are happy to receive cookies on the University of Southampton website.

×