Advanced

Reactivity of NHC Au(I)-C sigma-bonds with electrophiles. An investigation of their possible involvement in catalytic C-C bond formation

Johnson, Magnus LU ; van Rensburg, Jacobus LU ; Axelsson, Martin; Ahlquist, Marten S. G. and Wendt, Ola LU (2011) In Chemical Science 2(12). p.2373-2377
Abstract
The first example of the reaction of an isolated gold(I) complex with an aryl halide to form a C-C bond is reported. The reactivity of (NHC) Au(I)-R complexes towards a wide range of electrophiles was investigated. The Au-C sigma-bond is shown to exhibit low nucleophilicity, but it is reactive towards MeI and MeOTf to form toluene, biphenyl and ethane, most likely through an oxidative mechanism. Carbon dioxide is completely unreactive. The experimental findings are supported by theoretical calculations.
Please use this url to cite or link to this publication:
author
organization
publishing date
type
Contribution to journal
publication status
published
subject
in
Chemical Science
volume
2
issue
12
pages
2373 - 2377
publisher
Royal Society of Chemistry
external identifiers
  • wos:000296745500013
  • scopus:84859148194
ISSN
2041-6539
DOI
10.1039/c1sc00428j
language
English
LU publication?
yes
id
acde64cc-578f-427a-bd3d-26015b020227 (old id 2253367)
date added to LUP
2011-12-20 13:58:18
date last changed
2017-10-01 03:18:26
@article{acde64cc-578f-427a-bd3d-26015b020227,
  abstract     = {The first example of the reaction of an isolated gold(I) complex with an aryl halide to form a C-C bond is reported. The reactivity of (NHC) Au(I)-R complexes towards a wide range of electrophiles was investigated. The Au-C sigma-bond is shown to exhibit low nucleophilicity, but it is reactive towards MeI and MeOTf to form toluene, biphenyl and ethane, most likely through an oxidative mechanism. Carbon dioxide is completely unreactive. The experimental findings are supported by theoretical calculations.},
  author       = {Johnson, Magnus and van Rensburg, Jacobus and Axelsson, Martin and Ahlquist, Marten S. G. and Wendt, Ola},
  issn         = {2041-6539},
  language     = {eng},
  number       = {12},
  pages        = {2373--2377},
  publisher    = {Royal Society of Chemistry},
  series       = {Chemical Science},
  title        = {Reactivity of NHC Au(I)-C sigma-bonds with electrophiles. An investigation of their possible involvement in catalytic C-C bond formation},
  url          = {http://dx.doi.org/10.1039/c1sc00428j},
  volume       = {2},
  year         = {2011},
}