Jump to main content
Jump to site search

Issue 9, 2016
Previous Article Next Article

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

Author affiliations

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

Back to tab navigation

Supplementary files

Article information


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

Chem. Sci., 2016,7, 6190-6196
Article type
Edge Article
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. Material from this article can be used in other publications provided that the correct acknowledgement is given with the reproduced material.

Reproduced material should be attributed as follows:

  • For reproduction of material from NJC:
    [Original citation] - Published by The Royal Society of Chemistry (RSC) on behalf of the Centre National de la Recherche Scientifique (CNRS) and the RSC.
  • For reproduction of material from PCCP:
    [Original citation] - Published by the PCCP Owner Societies.
  • For reproduction of material from PPS:
    [Original citation] - Published by The Royal Society of Chemistry (RSC) on behalf of the European Society for Photobiology, the European Photochemistry Association, and RSC.
  • For reproduction of material from all other RSC journals:
    [Original citation] - Published by The Royal Society of Chemistry.

Information about reproducing material from RSC articles with different licences is available on our Permission Requests page.


Social activity

Search articles by author

Spotlight

Advertisements