Issue 9, 2016

Nucleophile promoted gold redox catalysis with diazonium salts: C–Br, C–S and C–P bond formation through catalytic Sandmeyer coupling

Abstract

Gold-catalyzed C-heteroatom (C–X) coupling reactions are evaluated without using sacrificial oxidants. Vital to the success of this methodology is the nucleophile-assisted activation of aryldiazonium salts, which could be an effective oxidant for converting Au(I) to Au(III) even without the addition of an assisting ligand or photocatalyst. By accelerating the reaction kinetics to outcompete C–C homo-coupling or diazonium dediazoniation, gold-catalyzed Sandmeyer reactions were achieved with different nucleophiles, forming C–Br, C–S and C–P bonds in high yields and selectivities.

Graphical abstract: Nucleophile promoted gold redox catalysis with diazonium salts: C–Br, C–S and C–P bond formation through catalytic Sandmeyer coupling

Supplementary files

Article information

Article type
Edge Article
Submitted
20 Apr 2016
Accepted
09 Jun 2016
First published
10 Jun 2016
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., 2016,7, 6190-6196

Author version available

Nucleophile promoted gold redox catalysis with diazonium salts: C–Br, C–S and C–P bond formation through catalytic Sandmeyer coupling

H. Peng, R. Cai, C. Xu, H. Chen and X. Shi, Chem. Sci., 2016, 7, 6190 DOI: 10.1039/C6SC01742H

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.

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