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Palladium(II) acetate catalyzed efficient synthesis of N ‐aryl‐α,β‐unsaturated amides via carbonylative addition of aniline derivatives to aromatic alkynes
Author(s) -
Ali Bassam El,
Tijani Jimoh,
ElGhanam Abdel Moneim
Publication year - 2002
Publication title -
applied organometallic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.53
H-Index - 71
eISSN - 1099-0739
pISSN - 0268-2605
DOI - 10.1002/aoc.317
Subject(s) - chemistry , aniline , catalysis , phosphine , aryl , palladium , carbonylation , medicinal chemistry , ligand (biochemistry) , organic chemistry , carbon monoxide , biochemistry , alkyl , receptor
A series of new N ‐aryl‐α,β‐disubstituted amides ( gem or E1; trans or E2 ) were synthesized in good yields by carbonylative addition of aniline derivatives 1a–f to aromatic alkynes 2a,b catalyzed by Pd(OAc) 2 and 1,3‐bis(diphenylphosphino)propane. The catalytic synthesis of tertiary α,β‐unsaturated amides was also successfully achieved. Traces of products were observed in the absence of p ‐toluenesulfonic acid used as an additive. The reaction is sensitive to the type of phosphine ligand and solvent. Copyright © 2002 John Wiley & Sons, Ltd.