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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.

SUBMITTER: He Z

PROVIDER: S-EPMC8150100 | biostudies-literature | 2020 Jan

REPOSITORIES: biostudies-literature

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Sulfoxide-mediated oxidative cross-coupling of phenols.

He Zhen Z Perry Gregory J P GJP Procter David J DJ

Chemical science 20200115 7

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. ...[more]

PMID: 34123295

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