Axial Coordination of NHC Ligands on Dirhodium(II) Complexes: Generation of a New Family of Catalysts
The Journal of Organic Chemistry2008Vol. 73(11), pp. 4076–4086
Citations Over TimeTop 10% of 2008 papers
Alexandre F. Trindade, Pedro M. P. Góis, Luı́s F. Veiros, Vânia André, M. Teresa Duarte, Carlos A. M. Afonso, Stephen Caddick, F. Geoffrey N. Cloke
Abstract
An efficient new methodology for the arylation of aldehydes is disclosed which uses dirhodium(II) catalysts and N-heterocyclic carbene (NHC) ligands. Complexes of Rh 2(OAc) 4 with one and two NHCs attached on the axial positions were successfully isolated, fully characterized, and used as catalysts in the reaction. The saturated monocomplex ((NHC 5)Rh 2(OAc) 4) 31 was shown to be the most active catalyst and was particularly efficient in the arylation of alkyl aldehydes. DFT calculations support participation of complexes with one axial NHC in the reaction as the catalysts active species and indicate that hydrogen bonds involving dirhodium unit, reactants, and solvent (alcohol) play an important role on the reaction mechanism.
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