Sulfoxide-mediated oxidative cross-coupling of phenols

Zhen He; Gregory J. P. Perry; David J. Procter

doi:10.1039/C9SC05668H

Sulfoxide-mediated oxidative cross-coupling of phenols

Zhen He, Gregory J. P. Perry, David J. Procter

Research output: Contribution to journal › Article › peer-review

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.

Original language	English
Journal	Chemical Science
Early online date	15 Jan 2020
DOIs	https://doi.org/10.1039/C9SC05668H
Publication status	Published - 2020

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title = "Sulfoxide-mediated oxidative cross-coupling of phenols",

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.",

author = "Zhen He and Perry, {Gregory J. P.} and Procter, {David J.}",

year = "2020",

doi = "10.1039/C9SC05668H",

language = "English",

journal = "Chemical Science",

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publisher = "Royal Society of Chemistry",

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T1 - Sulfoxide-mediated oxidative cross-coupling of phenols

AU - He, Zhen

AU - Perry, Gregory J. P.

AU - Procter, David J.

PY - 2020

Y1 - 2020

N2 - 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.

AB - 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.

U2 - 10.1039/C9SC05668H

DO - 10.1039/C9SC05668H

M3 - Article

SN - 2041-6520

JO - Chemical Science

JF - Chemical Science

ER -

Sulfoxide-mediated oxidative cross-coupling of phenols

Abstract

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