Palladium-catalyzed insertion of ethylene and 1,1-disubstituted difunctional olefins: an experimental and computational study

TitlePalladium-catalyzed insertion of ethylene and 1,1-disubstituted difunctional olefins: an experimental and computational study
Publication TypeJournal Article
Year of Publication2020
AuthorsGaikwad, SR, Patel, K, Deshmukh, SS, Mote, NR, Birajdar, RS, Pandole, SP, Chugh, J, Chikkali, SH
JournalChemPlusChem
Volume85
Issue6
Pagination1200-1209
Date PublishedJUN
Type of ArticleArticle
ISSN2192-6506
KeywordsHomogeneous catalysis, insertion copolymerization, Olefins, Palladium, Polyethylene
Abstract

Insertion or coordination copolymerization of ethylene with di-substituted olefins is challenging and the choice of di-substituted mono-functional olefin versus di-substituted di-functional olefin (DDO) appears to be decisive. Here we show that DDO-inserted species are amenable to ethylene insertion and polymerization. DDOs such as 2-acetamidoacrylic acid (AAA), methyl 2-acetamidoacrylate (MAAA), and ethyl 2-cyanoacrylate (ECA) were treated with palladium complex [{P perpendicular to O}PdMe(L)] (P perpendicular to O=kappa(2)-P,O-Ar2PC6H4SO2O with Ar=2-MeOC6H4; L=C2H6OS) and the existence of respective insertion intermediates in moderate yield (up to 37 %) was established. These intermediates were exposed to ethylene and corresponding ethylene-inserted products were isolated and characterized. A careful comparison with three model compounds confirmed ethylene insertion and polymerization. Thus, the combined experimental and computational investigations show that DDO-inserted species can undergo ethylene insertion and polymerization.

DOI10.1002/cplu.202000309
Type of Journal (Indian or Foreign)

Foreign

Impact Factor (IF)

2.753

Divison category: 
Central NMR Facility
Polymer Science & Engineering

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