Triazole-based leaving group for raft-mediated polymerization synthesized via the cu-mediated huisgen 1,3-dipolar cycloaddition reaction

Akeroyd N. ; Pfukwa R. ; Klumperman B. (2009)


A new RAFT agent leaving group based on a triazole moiety is introduced. The triazole moiety plays an active role in the stabilization of the intermediate radical, comparable to the phenyl group in a benzyl leaving group. The newly developed leaving group allows easy conjugation to a large variety of substrates where the triazole linking group is hydrolytically stable. Good control is reported in the polymerizations of vinyl acetate, N-vinylpyrrolidone, n-butyl acrylate, and styrene. The versatility of the method is exemplified by linking the triazole to a phenyl and to an oligosaccharide substrate. Overall, this new RAFT agent leaving group is a useful addition to the limited set of leaving groups reported in literature. © 2009 American Chemical Society.

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