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N-Heterocyclic carbenes (NHCs) as organocatalysts and structural components in metal-free polymer synthesis

Fèvre, Maréva, Pinaud, Julien, Gnanou, Yves, Vignolle, Joan, Taton, Daniel·2013·Chemical Society Reviews
DOI 10.1039/c2cs35383k
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Abstract

The chemistry of N-heterocyclic carbenes (NHCs) has witnessed tremendous development in the past two decades: NHCs have not only become versatile ligands for transition metals, but have also emerged as powerful organic catalysts in molecular chemistry and, more recently, in metal-free polymer synthesis. To understand the success of NHCs, this review first presents the electronic properties of NHCs, their main synthetic methods, their handling, and their reactivity. Their ability to activate key functional groups (e.g. aldehydes, esters, heterocycles, silyl ketene acetals, alcohols) is then discussed in the context of molecular chemistry. Focus has been placed on the activation of substrates finding analogies with monomers (e.g. bis-aldehydes, multi-isocyanates, cyclic esters, epoxides, N-carboxyanhydrides, etc.) and/or initiators (e.g. hydroxy- or trimethylsilyl-containing reagents) employed in such "organopolymerisation" reactions utilizing NHCs. A variety of metal-free polymers, including aliphatic polyesters and polyethers, poly(α-peptoid)s, poly(meth)acrylates, polyurethanes, or polysiloxanes can be obtained in this way. The last section covers the use of NHCs as structural components of the polymer chain. Indeed, NHC-based photoinitiators, chain transfer agents or functionalizing agents, as well as bifunctional NHC monomer substrates, can also serve for metal-free polymer synthesis.

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Metadata

Authors
Fèvre, M., Pinaud, J., Gnanou, Y., Vignolle, J., & Taton, D.
Venue
Chemical Society Reviews
Publisher
Royal Society of Chemistry (RSC)
Published
2013
Volume
42
Issue
5
Pages
2142
ISSN
  • 0306-0012 (ISSN-L)
  • 1460-4744
DOI
10.1039/c2cs35383k
OpenAlex
W2113057417
Cited by
532
References
5
FWCI
2.15
Type
journal article
Language
en
Open access
closed

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