B. Ali, J. Tijani, Abdel Munhem El-Ghanam
Sep 9, 2002
Citations
0
Influential Citations
28
Citations
Journal
Journal of Molecular Catalysis A-chemical
Abstract
Abstract The carbonylative coupling of 1-heptyne ( 1a ) with aniline ( 2a ) has been successfully achieved in the presence of Pd(OAc) 2 and a suitable bidentate phosphine ligand and solvent. The gem -α,β-unsaturated amide ( 3aa ) was formed as a predominant product in the presence of the catalytic system Pd(OAc) 2 /1,3-bis(diphenylphosphino)propane (dppp)/ p -toluenesulfonic acid ( p -TsOH)/CO in THF as a solvent. While the use Pd(OAc) 2 and 1,4-bis(diphenylphosphino)butane (dppb), under syngas (CO/H 2 ) conditions and in CH 2 Cl 2 as a solvent, affords the trans -α,β-unsaturated amide ( 4aa ) as the major product. A minor cyclic product ( 5aa ) was formed via the double carbonylation reaction. The regioselective carbonylative coupling reaction was also successfully applied to N -methyl aniline ( 2b ) with 1-heptyne ( 1a ) producing excellent yields of tertiary unsaturated amides.