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Suzuki reaction catalysed by a PCsp3P pincer Pd(II) complex: Evidence for a mechanism involving molecular species

Olsson, Daniel LU and Wendt, Ola LU (2009) In Journal of Organometallic Chemistry 694(19). p.3112-3115
Abstract
{Cis-1,3-bis[(di-tert-butylphosphino)methyl]cyclohexyl}palladium(II)trif luoroacetate (1) acts as a precatalyst for the Suzuki reaction of aryl halides with phenylboronic acid in the absence or presence of mercury to give the product in modest to reasonably good yields. The reaction was monitored by P-31- and H-1 NMR spectroscopy in a stepwise fashion, concluding that complex 1 reacts with activated boronic acids in the first reaction step to yield the corresponding phenyl complex 2. Complex 2 thereafter generates the Suzuki cross-coupling product upon addition of aryl halide. This shows that (PCP)Pd complexes, in addition to the previously demonstrated Pd(0)/Pd(II) mechanism, can mediate cross-coupling reactions using molecular species in... (More)
{Cis-1,3-bis[(di-tert-butylphosphino)methyl]cyclohexyl}palladium(II)trif luoroacetate (1) acts as a precatalyst for the Suzuki reaction of aryl halides with phenylboronic acid in the absence or presence of mercury to give the product in modest to reasonably good yields. The reaction was monitored by P-31- and H-1 NMR spectroscopy in a stepwise fashion, concluding that complex 1 reacts with activated boronic acids in the first reaction step to yield the corresponding phenyl complex 2. Complex 2 thereafter generates the Suzuki cross-coupling product upon addition of aryl halide. This shows that (PCP)Pd complexes, in addition to the previously demonstrated Pd(0)/Pd(II) mechanism, can mediate cross-coupling reactions using molecular species in a non-zero oxidation state. (C) 2009 Elsevier B.V. All rights reserved. (Less)
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author
organization
publishing date
type
Contribution to journal
publication status
published
subject
keywords
Pincer ligands, Palladium, Cross-coupling, NMR studies
in
Journal of Organometallic Chemistry
volume
694
issue
19
pages
3112 - 3115
publisher
Elsevier
external identifiers
  • wos:000268799500009
  • scopus:68049129702
ISSN
0022-328X
DOI
10.1016/j.jorganchem.2009.05.025
language
English
LU publication?
yes
id
4ec1b118-d1cf-4949-b97a-80ee151bc666 (old id 1478232)
date added to LUP
2009-09-23 09:21:18
date last changed
2017-08-13 04:10:02
@article{4ec1b118-d1cf-4949-b97a-80ee151bc666,
  abstract     = {{Cis-1,3-bis[(di-tert-butylphosphino)methyl]cyclohexyl}palladium(II)trif luoroacetate (1) acts as a precatalyst for the Suzuki reaction of aryl halides with phenylboronic acid in the absence or presence of mercury to give the product in modest to reasonably good yields. The reaction was monitored by P-31- and H-1 NMR spectroscopy in a stepwise fashion, concluding that complex 1 reacts with activated boronic acids in the first reaction step to yield the corresponding phenyl complex 2. Complex 2 thereafter generates the Suzuki cross-coupling product upon addition of aryl halide. This shows that (PCP)Pd complexes, in addition to the previously demonstrated Pd(0)/Pd(II) mechanism, can mediate cross-coupling reactions using molecular species in a non-zero oxidation state. (C) 2009 Elsevier B.V. All rights reserved.},
  author       = {Olsson, Daniel and Wendt, Ola},
  issn         = {0022-328X},
  keyword      = {Pincer ligands,Palladium,Cross-coupling,NMR studies},
  language     = {eng},
  number       = {19},
  pages        = {3112--3115},
  publisher    = {Elsevier},
  series       = {Journal of Organometallic Chemistry},
  title        = {Suzuki reaction catalysed by a PCsp3P pincer Pd(II) complex: Evidence for a mechanism involving molecular species},
  url          = {http://dx.doi.org/10.1016/j.jorganchem.2009.05.025},
  volume       = {694},
  year         = {2009},
}