Reactivity of NHC Au(I)-C sigma-bonds with electrophiles. An investigation of their possible involvement in catalytic C-C bond formation
(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:
https://lup.lub.lu.se/record/2253367
- author
- Johnson, Magnus LU ; van Rensburg, Jacobus LU ; Axelsson, Martin ; Ahlquist, Marten S. G. and Wendt, Ola LU
- organization
- publishing date
- 2011
- 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
- additional info
- The information about affiliations in this record was updated in December 2015. The record was previously connected to the following departments: Organic chemistry (S/LTH) (011001240)
- id
- acde64cc-578f-427a-bd3d-26015b020227 (old id 2253367)
- date added to LUP
- 2016-04-01 10:34:30
- date last changed
- 2022-04-12 07:35:17
@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}}, doi = {{10.1039/c1sc00428j}}, volume = {{2}}, year = {{2011}}, }