Journal of Molecular Catalysis A-Chemical, Vol.245, No.1-2, 248-254, 2006
Active catalysts for the Suzuki coupling: Palladium complexes of tetrahydropyrimid-2-ylidenes
An alternative way to synthesize a mixed N-heterocyclic carbenes (NHC) phosphine palladium(II) complex is described in this work. A free carbene, generated by deprotonation of a tetrahydro-pyrimidinium salt, was reacted with Pd(PPh3)(2)Cl-2 to yield the desired mixed NHC phosphine palladium(II) complex. In this work, we have combined the superior activity of mixed NHC phosphine palladium complexes in Suzuki-coupling reactions with the additional advantage of a stronger or-donating ligand. The combination of these two effects results in an increased catalytic activity in Suzuki reactions than found for corresponding mixed imidazole-ylidene phosphine complexes. Using this new class of catalysts, TONs of approximately 1 Mio. after a reaction time of 14 h can be achieved. Desactivated bromoarenes could also be coupled efficiently, using quite a low amount of catalyst (0.005 mol%). Even aryl chlorides can be coupled: TONs of approximately 6000 can be reached after only 14 It without any detectable catalyst deterioration using only 0.01 mol% of catalyst. (c) 2005 Elsevier B.V. All rights reserved.
Keywords:N-heterocyclic carbene;tetrahydropyrimid-2-ylidene;palladium;Suzuki coupling;carbon-carbon bond formation