Issue 1, 2015

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

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

Supplementary files

Article information

Article type
Edge Article
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
Creative Commons BY license

Chem. Sci., 2015,6, 288-293

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

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements