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Cyclometallated gold(iii) aryl-pyridine complexes as efficient catalysts for three-component synthesis of substituted oxazoles.

von Wachenfeldt, Henrik LU ; Polukeev, Alexey LU ; Loganathan, Nagarajan LU ; Paulsen, Filip LU ; Röse, Philipp; Garreau, Marion; Wendt, Ola LU and Strand, Daniel LU (2015) In Dalton Transactions 44(12). p.5347-5353
Abstract
Cyclometallated aryl-pyridine gold(iii) complexes are shown to be efficient catalysts for the multicomponent reaction between N-benzyl imines, alkynes, and acyl chlorides to form trisubstituted oxazoles. The reaction typically proceeds in good yields (up to over 80%) and short reaction times (∼15 minutes). The high stability of the investigated cyclometallated catalysts enables a retained efficiency for this reaction in terms of rate and yield using as little as 0.5 mol% catalyst, a reduction by an order of magnitude compared to previously used Au(iii)-salen complexes. An attractive feature of the present catalytic system is that active catalysts can be formed from simple pre-catalysts under the reaction conditions. Both cyclometallated... (More)
Cyclometallated aryl-pyridine gold(iii) complexes are shown to be efficient catalysts for the multicomponent reaction between N-benzyl imines, alkynes, and acyl chlorides to form trisubstituted oxazoles. The reaction typically proceeds in good yields (up to over 80%) and short reaction times (∼15 minutes). The high stability of the investigated cyclometallated catalysts enables a retained efficiency for this reaction in terms of rate and yield using as little as 0.5 mol% catalyst, a reduction by an order of magnitude compared to previously used Au(iii)-salen complexes. An attractive feature of the present catalytic system is that active catalysts can be formed from simple pre-catalysts under the reaction conditions. Both cyclometallated and non-cyclometallated complexes were characterized in the solid state by single crystal X-ray diffraction. (Less)
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author
organization
publishing date
type
Contribution to journal
publication status
published
subject
in
Dalton Transactions
volume
44
issue
12
pages
5347 - 5353
publisher
Royal Society of Chemistry
external identifiers
  • pmid:25689826
  • wos:000351439200014
  • scopus:84924787805
ISSN
1477-9234
DOI
10.1039/c4dt03806a
language
English
LU publication?
yes
id
54846dc3-9a3c-4e86-b1e0-3432316bb3f7 (old id 5143450)
date added to LUP
2015-03-09 17:06:02
date last changed
2017-08-13 03:12:25
@article{54846dc3-9a3c-4e86-b1e0-3432316bb3f7,
  abstract     = {Cyclometallated aryl-pyridine gold(iii) complexes are shown to be efficient catalysts for the multicomponent reaction between N-benzyl imines, alkynes, and acyl chlorides to form trisubstituted oxazoles. The reaction typically proceeds in good yields (up to over 80%) and short reaction times (∼15 minutes). The high stability of the investigated cyclometallated catalysts enables a retained efficiency for this reaction in terms of rate and yield using as little as 0.5 mol% catalyst, a reduction by an order of magnitude compared to previously used Au(iii)-salen complexes. An attractive feature of the present catalytic system is that active catalysts can be formed from simple pre-catalysts under the reaction conditions. Both cyclometallated and non-cyclometallated complexes were characterized in the solid state by single crystal X-ray diffraction.},
  author       = {von Wachenfeldt, Henrik and Polukeev, Alexey and Loganathan, Nagarajan and Paulsen, Filip and Röse, Philipp and Garreau, Marion and Wendt, Ola and Strand, Daniel},
  issn         = {1477-9234},
  language     = {eng},
  number       = {12},
  pages        = {5347--5353},
  publisher    = {Royal Society of Chemistry},
  series       = {Dalton Transactions},
  title        = {Cyclometallated gold(iii) aryl-pyridine complexes as efficient catalysts for three-component synthesis of substituted oxazoles.},
  url          = {http://dx.doi.org/10.1039/c4dt03806a},
  volume       = {44},
  year         = {2015},
}