Syntheses of C1-symmetric bidentate ligands having pyridyl and 1,3-Thiazolyl, 1-methylimidazolyl or pyrazinyl donor groups for enantioselective palladium-catalyzed allylic substitution and copper-catalyzed cyclopropanation

Research output: Journal Publications and Reviews (RGC: 21, 22, 62)21_Publication in refereed journalpeer-review

21 Scopus Citations
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Author(s)

  • Pang-Fei Teng
  • Chui-Shan Tsang
  • Ho-Lun Yeung
  • Wing-Leung Wong
  • Wing-Tak Wong

Detail(s)

Original languageEnglish
Pages (from-to)5676-5684
Journal / PublicationJournal of Organometallic Chemistry
Volume691
Issue number26
Publication statusPublished - 15 Dec 2006

Abstract

New chiral C1-symmetric bidentate ligands, which possess two different nitrogen heterocycles, 1,3-thiazolyl, 1-methylimidazolyl or pyrazinyl and one pyridyl group, were prepared by Kröhnke condensation in 36-59% overall yield. Stable Pd(II)-allyl and Cu(II) chloride complexes formed by some of the ligands were obtained in 60-65% yields. X-ray crystal structure analysis of a copper(II) complex having 1-methylimidazolyl group indicated that it is a μ-chloro bridge dimer. The Pd(II)-allyl complexes were found to be active catalysts in the asymmetric allylic substitution of 1,3-diphenylprop-2-enyl acetate. The best result observed was 85% e.e. and 99% isolated yield. In addition, the in situ generated Cu(OTf)2 complexes were found to be active catalysts in cyclopropanation of styrene with ethyl diazoacetate. © 2006 Elsevier B.V. All rights reserved.

Research Area(s)

  • Allylic Substitution, Copper, Cyclopropanation, Palladium, Pyridyl

Citation Format(s)

Syntheses of C1-symmetric bidentate ligands having pyridyl and 1,3-Thiazolyl, 1-methylimidazolyl or pyrazinyl donor groups for enantioselective palladium-catalyzed allylic substitution and copper-catalyzed cyclopropanation. / Teng, Pang-Fei; Tsang, Chui-Shan; Yeung, Ho-Lun et al.

In: Journal of Organometallic Chemistry, Vol. 691, No. 26, 15.12.2006, p. 5676-5684.

Research output: Journal Publications and Reviews (RGC: 21, 22, 62)21_Publication in refereed journalpeer-review