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Investigation into thiol-(meth)acrylate Michael addition reactions using amine and phosphine catalysts

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Polymer Chemistry Vol - 1 Issue - 7

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Investigation into thiol-(meth)acrylate Michael addition reactions using amine and phosphine catalysts

Content Provider	Royal Society of Chemistry (RSC)
Author	Davis, Thomas P. Becer, C. Remzi Soeriyadi, Alexander H. Tong, Zhen Rees, Gregory Randev, Rajan K. Boyer, Cyrille Haddleton, David M. Li, Guang-Zhao
Copyright Year	2010
Abstract	This work describes a study into thiol–ene based Michael addition reactions. Different catalysts, primary and tertiary amines and phosphines, were investigated for the reaction of a range of thiols with dimers and oligomers of some (meth)acrylates. Primary and tertiary amines are efficient catalysts for the thiol–ene reaction, although these catalysts require several hours to reach high conversion. Moreover, the phosphine catalysts, dimethylphenylphosphine (DMPP) and tris-(2-carboxyethyl)phosphine (TCEP), were investigated in detail. DMPP is an efficacious catalyst yielding complete conversion in few minutes under optimized conditions. Importantly, the concentration of DMPP should be kept at catalytic levels to avoid the formation of by-products, originating from the addition of DMPP to the vinyl group. Furthermore, TCEP is an efficient catalyst for thiol–ene reactions in aqueous media when the pH of the medium is higher than 8.0 since at acidic pH the formation of by-products is observed.
Starting Page	1196
Ending Page	1204
Page Count	9
File Format	HTM / HTML PDF
ISSN	17599954
Volume Number	1
Issue Number	8
Journal	Polymer Chemistry
DOI	10.1039/c0py00100g
Language	English
Publisher	Royal Society of Chemistry
Access Restriction	Open
Subject Keyword	Dimethylphenylphosphine Phosphine Michael DMPP Vinyl group Michael reaction
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry Biochemistry Bioengineering Biomedical Engineering Polymers and Plastics

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