Catalytic Carbonyl Z-Dienylation via Multicomponent Reductive Coupling of Acetylene to Aldehydes and α-Ketoesters Mediated by Hydrogen: Carbonyl Insertion into Cationic Rhodacyclopentadienes
Jong Rock Kong and Michael J. Krische*
*Department of Chemistry and Biochemistry, University of Texas at Austin, Austin, Texas 78712, Email: mkrischemail.utexas.edu
J. R. Kong, M. J. Krische, J. Am. Chem. Soc., 2006, 128, 16040-16041.
DOI: 10.1021/ja0664786 (free Supporting Information)
Exposure of aldehydes or α-ketoesters to acetylene and hydrogen gas at ambient temperature and pressure in the presence of a cationic rhodium catalysts provides the products of a formal carbonyl Z-butadienylation. These multicomponent couplings represent the first use of acetylene gas in metal-catalyzed reductive C-C bond formation.
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E. Skucas, J. R. Kong, M. J. Krische, J. Am. Chem. Soc., 2007, 129, 7242-7243.