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Catalytic and regioselective synthesis of gem‐ or trans‐α,β‐unsaturated amides by carbonylation of alkyl alkynes with aniline derivatives by palladium(II) and phosphine
Author(s) -
El Ali Bassam,
Tijani Jimoh
Publication year - 2003
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.548
Subject(s) - chemistry , phosphine , catalysis , carbonylation , regioselectivity , medicinal chemistry , aniline , alkyl , palladium , ligand (biochemistry) , denticity , organic chemistry , propane , carbon monoxide , biochemistry , receptor , crystal structure
The reaction of carbonylative addition of alkyl alkynes to aniline derivatives has been successfully achieved by a catalytic system formed of Pd(OAc) 2 and a suitable bidentate phosphine ligand. The reaction led mainly to gem‐α,β‐unsaturated amides ( 3 ) with Pd(OAc) 2 /1,3‐bis(diphenylphosphino)propane/ p ‐toluenesulfonic acid/CO as the catalytic system. However, the reaction catalyzed by Pd(OAc) 2 /1,4‐bis(diphenylphosphino)butane/H 2 /CO in CH 2 Cl 2 as a solvent affords trans‐α,β‐unsaturated amides ( 4 ) as the major product. Copyright © 2003 John Wiley & Sons, Ltd.