Tripodal N-heterocyclic carbene complexes of palladium and copper: Syntheses, characterization, and catalytic activity

Reference:

Ellul, C. E., Reed, G., Mahon, M. F., Pascu, S. I. and Whittlesey, M. K., 2010. Tripodal N-heterocyclic carbene complexes of palladium and copper: Syntheses, characterization, and catalytic activity. Organometallics, 29 (18), pp. 4097-4104.

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Official URL:

http://dx.doi.org/10.1021/om100758x

Abstract

The tris-palladium tripodal N-heterocyclic carbene (NHC) complexes (timtebtBu){Pd(ICy)I2}3 (4a), (timteb tBu){Pd(PPh3)I2}3 (5a), and (timtebdipp){Pd(PPh3)I2}3 (5b) (timtebtBu = 1,3,5-{tris(tert-butylimidazol-2-ylidene)methyl}-2,4,6- triethylbenzene, 3a; ICy = 1,3-dicyclohexylimidazol-2-ylidene; timteb dipp = 1,3,5-{tris({2,6-diisopropylphenyl}imidazol-2-ylidene)methyl}- 2,4,6-triethylbenzene, 3b) were prepared by reaction of Pd(II) precursors with either the free carbenes or imidazolium salts. Treatment of [Cu(NCMe) 4]X (X = PF6, BF4) with 3a or 3b produced the tris-copper(I) bridged complexes [(timtebR) Cu3(3-O)]X (R = tBu, X = PF6, 6a; R = dipp, X = BF4, 6b). Complexes 4a, 5a, and 6a were structurally characterized. The palladium complexes were tested as catalysts for Suzuki-Miyaura and Sonogashira coupling reactions and the copper species also employed for the Sonogashira reaction, as well as for the Ullmann-type arylation of imidazoles and phenols.

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