Issue 8, 2010

Investigation into thiol-(meth)acrylateMichael addition reactions using amine and phosphinecatalysts

Abstract

This work describes a study into thiolene 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 thiolene 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 thiolene 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.

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

Supplementary files

Article information

Article type
Paper
Submitted
26 3 2010
Accepted
03 5 2010
First published
07 6 2010

Polym. Chem., 2010,1, 1196-1204

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

G. Li, R. K. Randev, A. H. Soeriyadi, G. Rees, C. Boyer, Z. Tong, T. P. Davis, C. R. Becer and D. M. Haddleton, Polym. Chem., 2010, 1, 1196 DOI: 10.1039/C0PY00100G

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