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Issue 1, 2015
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Stoichiometric to catalytic reactivity of the aryl cycloaurated species with arylboronic acids: insight into the mechanism of gold-catalyzed oxidative C(sp2)–H arylation

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Abstract

Based on the well-defined five-membered aryl gold(III) complexes, [Au(tpy)X2] (3a and 3b) and [AuBr(Ph)(tpy)] (7), as well as the aryl gold(III) complex [AuCl2(Ph)(tpy)] (8) (tpy = 2-(o-tolyl)pyridine) as reliable models, we present a detailed study of the mechanism for gold(III)-catalyzed oxidative cross-coupling reactions between cycloaurable arenes and arylboronic acids. Here we report the direct evidence for a mechanistic proposal including arene C–H activation, transmetallation and biaryl reductive elimination. The chelation-assisted C–H activation strategy has been used for the development of the gold(III)-catalyzed C–H bond arylation of arenes with aryl reagents to forge extended π-conjugated systems.

Graphical abstract: Stoichiometric to catalytic reactivity of the aryl cycloaurated species with arylboronic acids: insight into the mechanism of gold-catalyzed oxidative C(sp2)–H arylation

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Supplementary files

Article information


Submitted
13 Jul 2014
Accepted
07 Oct 2014
First published
09 Oct 2014

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2015,6, 288-293
Article type
Edge Article
Author version available

Stoichiometric to catalytic reactivity of the aryl cycloaurated species with arylboronic acids: insight into the mechanism of gold-catalyzed oxidative C(sp2)–H arylation

Q. Wu, C. Du, Y. Huang, X. Liu, Z. Long, F. Song and J. You, Chem. Sci., 2015, 6, 288
DOI: 10.1039/C4SC02070G

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