Mono-, bis- and tris-piperidine fused imidazolinium salts: their in situ catalytic applications for C-C bond formation in aqueous solutions


TÜRKMEN H. , CAN R., CETINKAYA B.

APPLIED ORGANOMETALLIC CHEMISTRY, vol.23, no.9, pp.365-369, 2009 (Journal Indexed in SCI) identifier identifier

  • Publication Type: Article / Article
  • Volume: 23 Issue: 9
  • Publication Date: 2009
  • Doi Number: 10.1002/aoc.1520
  • Title of Journal : APPLIED ORGANOMETALLIC CHEMISTRY
  • Page Numbers: pp.365-369

Abstract

The 1,5,6,7,8,8a-hexahydroimidazo[1,5-a]pyridine, 3, was quaternized with 2-(bromomethyl-1,3,5-trimethyl benzene, 1,4-bis(bromomethyl)-2,3,5,6-tetramethylbenzene, 2,4-bis(bromomethyl)-1,3,5-trimethylbenzene, 1,3,5-tris(bromomethyl)-2,4,6-trimethylbenzene and 1,3,5-tris(bromomethyl)-2,4,6-triethylbenzene to obtain mono-, bis- and tris-imidazolinium salts (4-7) which were characterized by elemental analysis and NMR spectroscopy. In order to understand the effects of these changes on the N-substituent and how they translate to catalytic activity, these new salts (4-7) with Pd(OAc)(2) were applied as in situ catalysts for Suzuki-Miyaura and Heck-Mirozoki cross-coupling reactions of aryl chlorides and aryl bromides, respectively. The tris-imidazolinium salts (7) were found to be more efficient than the related analogs 4-6. Copyright (C) 2009 John Wiley& Sons, Ltd.