Ortho, ortho′-Substituted KITPHOS monophosphines: Highly efficient ligands for palladium-catalyzed C-C and C-N bond formation

Academic Article

Abstract

  • ortho, ortho′-Substitution of the phosphinoalkyne-derived aryl ring in KITPHOS (11-dicyclohexylphosphino-12-phenyl-9,10-ethenoanthracene) monophosphines enhances the performance of this class of ligand in palladium-catalyzed Suzuki-Miyaura cross-couplings and BuchwaldHartwig aminations, compared with their unsubstituted and mono-substituted counterparts. An alternative complementary synthesis of KITPHOS monophosphines has been developed and two new members of this family, 2,6-Me 2 -KITPHOS [11-dicyclohexylphosphino-12-(2,6-dimethylphenyl)-9,10-ethenoanthracene] and 2,6-(MeO) 2 -KITPHOS [11-dicyclohexylphosphino-12-(2,6-dimethoxyphenyl)-9,10-ethenoanthracene], have been prepared; palladium complexes of both are highly efficient catalysts for C - C and C - N bond formation with a range of electron-rich and electron-poor aromatic chlorides as well as heteroaryl chlorides. © 2010 Wiley-VCH Verlag GmbH & Co. KGaA.
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    Digital Object Identifier (doi)

    Author List

  • Doherty S; Knight JG; McGrady JP; Ferguson AM; Ward NAB; Harrington RW; Clegg W
  • Start Page

  • 201
  • End Page

  • 211
  • Volume

  • 352
  • Issue

  • 1