화학공학소재연구정보센터
Journal of Catalysis, Vol.365, 24-28, 2018
One-step palladium catalysed synthetic route to unsaturated pelargonic C-9-amides directly from 1,3-butadiene
The first example of the palladium catalysed amidotelomerisation is presented, in style of the ambitious carboxytelomerisation. A straightforward synthetic tool was generated to produce several industrial relevant pelargonic C-9-amides based on the fundamental chemical feedstocks: 1,3-butadiene, carbon monoxide and secondary amines. The reaction network was uncovered and crucial influences were determined by design of experiments (DoE). Through the incorporation of an auto-tandem palladium acetate/diphenylphosphino ethane catalytic system, very good yields up to 77% of the desired amides and excellent selectivities of carbonylation products of 94% were achieved. The application of the amidotelomerisation conditions to different classes of amines offered a broad range of the corresponding pelargonic C-9-amides. Understanding the tandem catalysis, significant inhibition factors were uncovered and through a stepwise optimisation, for the first time a carbonylation reaction of octadienyl amines (telomer products) was shown, yielding in 99% of the desired linear pelargonic C-9-amide. (C) 2018 Elsevier Inc. All rights reserved.