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Selective formation of α,ω-ester amides from the aminocarbonylation of castor oil derived methyl 10-undecenoate and other unsaturated substrates†
Cristina Jiménez-Rodriguez,Angel A. Núñez-Magro,Thomas Seidensticker,Graham R. Eastham,Marc R. L. Furst,David J. Cole-Hamilton
Catalysis Science & Technology Pub Date : 04/16/2014 00:00:00 , DOI:10.1039/C4CY00158C
Abstract

The reaction of long chain alkenes with CO and aniline in the presence of palladium complexes of 1,2-bis-(ditertbutylphosphinomethyl)benzene produces amides with high linear selectivity, with much higher rates and catalyst stability when 2-naphthol and sodium or potassium iodide are added. Unsaturated esters including methyl 10-undecenoate from castor oil give α,ω-ester amides, whilst reactions in THF give N-phenylpyrrolidine.

Graphical abstract: Selective formation of α,ω-ester amides from the aminocarbonylation of castor oil derived methyl 10-undecenoate and other unsaturated substrates
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