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Highly Selective Synthesis of Carboxamides via Transition Metal Catalysed Aminocarbonylation

[ Vol. 2 , Issue. 3 ]

Author(s):

Mercedesz Kiss, Attila Takacs and Laszlo Kollar   Pages 319 - 338 ( 20 )

Abstract:


This short review summarises the most important results obtained during the past decade in the field of palladium catalysed aminocarbonylation. In this reaction, using amines as N-nucleophiles, the carbonylation of enol-triflates/aryl-triflates or their synthetic surrogates, alkenyl halides/aryl halides takes place resulting in the formation of unsaturated carboxamides or aryl carboxamides. In the latter case, 2-ketocarboxamides are also formed via double carbon monoxide insertion. The efficiency of aminocarbonylation is illustrated by several high-yielding syntheses including transformation of both simple model substrates and skeletons of biological importance. As green chemistry aspects of this reaction, the ambient conditions, high activity, low catalyst loading, the possibility of tuning selectivities and high functional group tolerance should be mentioned.

Keywords:

Amide, carbonylation, palladium, chemoselectivity, environmentally benign reaction.

Affiliation:

University of Pecs, Ifjusag u. 6. (P. O. Box 266), H-7623 Pecs; Hungary.

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