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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:

J. R. Kong, M. J. Krische, J. Am. Chem. Soc., 2006, 128, 16040-16041.

DOI: 10.1021/ja0664786


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.

see article for more examples

Enantioselective Reductive Coupling of Acetylene to N-Arylsulfonyl Imines via Rhodium Catalyzed C-C Bond-Forming Hydrogenation: (Z)-Dienyl Allylic Amines

E. Skucas, J. R. Kong, M. J. Krische, J. Am. Chem. Soc., 2007, 129, 7242-7243.

Key Words

Allylic Alcohols, Dienes, Multicomponent Reactions, Hydrogen

ID: J48-Y2006-4030