Issue 22, 2018

Ultrafast and efficient aza- and thiol-Michael reactions on a polyester scaffold with internal electron deficient triple bonds

Abstract

A polyester scaffold possessing electron deficient triple bonds in the main chain was prepared and utilized as a precursor for aza- and thiol-Michael addition reactions. A variety of primary and secondary amines as well as thiol compounds were utilized in the reactions. Very high efficiencies were found for all Michael addition reactions in a reasonably short time (2 min). While aza-Michael addition reactions do not require any catalysts, thiol-Michael addition reactions could be performed in the presence of a catalyst. After a detailed catalyst search, 1,4-diazabicyclo[2.2.2]octane (DABCO) was found to be the most efficient catalyst for thiol-Michael addition reactions. It is also observed that when amidine and guanidine bases were utilized for thiol-Michael addition reactions, a second thiol addition appreciably occurred on the remaining double bonds. Besides, for the first time, one-pot and one-step heterofunctionalization on the polyester was performed either solely by aza-Michael addition reactions employing three or four different secondary amines, or by a combination of aza- and thiol-Michael addition reactions.

Graphical abstract: Ultrafast and efficient aza- and thiol-Michael reactions on a polyester scaffold with internal electron deficient triple bonds

Supplementary files

Article information

Article type
Paper
Submitted
28 Mar 2018
Accepted
01 May 2018
First published
02 May 2018

Polym. Chem., 2018,9, 3037-3054

Ultrafast and efficient aza- and thiol-Michael reactions on a polyester scaffold with internal electron deficient triple bonds

U. S. Gunay, M. Cetin, O. Daglar, G. Hizal, U. Tunca and H. Durmaz, Polym. Chem., 2018, 9, 3037 DOI: 10.1039/C8PY00485D

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