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-co...

Full description

Saved in:
Bibliographic Details
Published in:Chemical science (Cambridge) 2020-02, Vol.11 (7), p.21-25
Main Authors: He, Zhen, Perry, Gregory J. P, Procter, David J
Format: Article
Language:English
Subjects:
Aromatic compounds
Chemistry
Cross coupling
Crystallography
Diketones
NMR
Nuclear magnetic resonance
Nucleophiles
Oligomers
Phenols
Selectivity
Sulfoxides
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary: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. A metal-free, oxidative coupling of phenols with various nucleophiles, including arenes, 1,3-diketones and other phenols, is reported.
ISSN:2041-6520
2041-6539
DOI:10.1039/c9sc05668h