NDLI: Azolium hydrogen carbonates and azolium carboxylates as organic pre-catalysts for N-heterocyclic carbene-catalysed group transfer and ring-opening polymerisations

Content Provider	Royal Society of Chemistry (RSC)
Author	Vignolle, Joan Taton, Daniel Fèvre, Maréva
Copyright Year	2013
Abstract	Various imidazolium-2-carboxylates and (benz)imidazolium hydrogen carbonates, denoted as NHC–CO2 adducts and [NHC(H)][HCO3], respectively, were employed as masked N-heterocyclic carbenes (NHCs) to bring about both the ring opening polymerisation (ROP) of D,L-lactide (LA) and the group transfer polymerisation (GTP) of methyl methacrylate (MMA). Polymerisation reactions could be performed at room temperature by generation of related free NHCs by a simple solvation effect. Catalytic efficiencies of imidazolium-2-carboxylates were found to be approximately three times higher than that of their hydrogen carbonate counterparts for the ROP of D,L-LA, except in the particular case of 1,3-dicyclohexylbenzimidazolium hydrogen carbonate that exhibited a similar catalytic performance to that of NHC–CO2 adducts. The catalytic efficiencies of free NHCs and NHC precursors were thus in the following order: [NHC(H)][HCO3] < NHC–CO2 adducts ≪ free NHCs. Only NHC–CO2 adducts allowed the catalysis of the GTP of MMA in bulk in a controlled manner, [NHC(H)][HCO3] precursor salts being poorly soluble in the monomer substrate, causing a loss of control of GTP under solvent-less conditions.
Starting Page	1995
Ending Page	2003
Page Count	9
File Format	HTM / HTML PDF
ISSN	17599954
Volume Number	4
Issue Number	6
Journal	Polymer Chemistry
DOI	10.1039/c2py20915b
Language	English
Publisher	Royal Society of Chemistry
Access Restriction	Open
Subject Keyword	MMA Bicarbonate Persistent carbene Guanosine triphosphate Solvation Los Angeles Methyl methacrylate Monomer ROP of Hydrogen bond
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry Biochemistry Bioengineering Biomedical Engineering Polymers and Plastics

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