Journal
INORGANICA CHIMICA ACTA
Volume 363, Issue 9, Pages 1979-1983Publisher
ELSEVIER SCIENCE SA
DOI: 10.1016/j.ica.2009.02.035
Keywords
N-Heterocyclic carbenes; Palladium; Thiophene; Suzuki-Miyaura reaction; Homogeneous catalysis
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Funding
- National University of Singapore [R 143-000-327-133]
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A new thiophene-functionalized benzimidazolium salt (2) has been prepared by reacting N-methylbenzimidazole with 2-bromomethylthiophene (1), which in turn was obtained by bromination of 2-thiophenemethanol with PBr3. Subsequent reaction of salt 2 with Pd(OAc)(2) afforded the cis-configured bis(carbene) Pd(II) complex (cis-3), which in solution exists as an inseparable mixture of cis-anti and cis-syn-rotamers in a 3.5:1 ratio. All new compounds have been fully characterized by spectroscopic and spectrometric methods. A preliminary catalytic study shows that cis-3 is highly active in the Suzuki-Miyaura coupling of aryl bromides with phenylboronic acid in/on water as environmentally benign reaction media. (C) 2009 Elsevier B.V. All rights reserved.
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