A new library of arsine, stibine-stabilized N-heterocyclic carbene palladium complexes: synthesis, structures and activities in C-C and C-N coupling reactions.

Abstract

A series of new N-heterocyclic carbene palladium complexes bearing AsPh3 and SbPh3 functions PdCl2(IMes)(AsPh3) (1a), PdCl2(IMes)(SbPh3) (1b), PdCl2(IPr)(AsPh3) (1c), PdCl2(IPr)(SbPh3) (1d), PdCl2(SIMes)(AsPh3) (2a), PdCl2(SIMes)(SbPh3) (2b), PdCl2(SIPr)(AsPh3) (2c), and PdCl2(SIPr)(SbPh3) (2d) (IMes = N,N'-bis-(2,4,6-trimethylphenyl)imidazol-2-ylidene; IPr = N,N'-bis-(2,6-di(iso-propyl)phenyl)imidazol-2-ylidene; SIMes = N,N'-bis-(2,4,6-trimethylphenyl)imidazolidin-2-ylidene; SIPr = N,N'-bis-(2,6-di(iso-propyl)phenyl)imidazolidin-2-ylidene) was synthesized and fully characterized by (1)H NMR, (13)C NMR, and FT-IR spectroscopy, elemental analysis and single-crystal X-ray crystallography. The catalytic potential of these arsine and stibine-stabilized carbene palladium complexes for Pd-mediated transformations was investigated with various substrates in the Hiyama cross-coupling reactions and Buchwald-Hartwig aminations. The results demonstrate that these complexes show high catalytic activity and good tolerance to various chemical functions.