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Issue 13, 2019
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The mechanistic duality of (thio)urea organocatalysts for ring-opening polymerization

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Abstract

Among the various catalysts for ROP, H-bonding organocatalysts stand out in the precise level of reaction control they are able to render during ROP. The H-bonding class of organocatalysts are thought to effect ROP via dual activation of both monomer and chain end. (Thio)urea mediated ROP has experienced a renaissance as a new polymerization mechanism – mediated by imidate or thioimidate species – facilitates new modes of reactivity and new synthetic abilities. Indeed, the urea class of H-bond donors has been shown to be more active than their corresponding thioureas. The imidate mechanism remains highly active in polar solvents and exhibits remarkable control – and ‘living’ behavior – under solvent-free conditions, and a broad range of temperatures is accessible. The advancements in synthetic abilities have all evolved through a greater understanding of reaction mechanism. Through the continued synergistic advances of catalysis and material, the (thio)urea class of catalyst can find use in a host of potential applications, research and industrial environments.

Graphical abstract: The mechanistic duality of (thio)urea organocatalysts for ring-opening polymerization

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Article information


Submitted
21 Dec 2018
Accepted
25 Feb 2019
First published
05 Mar 2019

Org. Biomol. Chem., 2019,17, 3305-3313
Article type
Review Article
Author version available

The mechanistic duality of (thio)urea organocatalysts for ring-opening polymerization

N. U. Dharmaratne, J. U. Pothupitiya and M. K. Kiesewetter, Org. Biomol. Chem., 2019, 17, 3305
DOI: 10.1039/C8OB03174F

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