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Issue 43, 2018
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Polycondensation of methacrylates: auto-tandem organocatalysis using N-heterocyclic carbenes

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Abstract

The first polycondensations of methacrylates have been realized by auto-tandem N-heterocyclic carbene (NHC) catalysis comprising transesterification and tail-to-tail dimerization. The single NHC catalyst promoted self-polycondensation of hydroxy-functionalized methacrylates and direct polycondensation of n-butyl methacrylate (nBMA) with diols to synthesize new unsaturated polyesters. The self-polycondensation efficiently produced polyesters in high yields. The short-time polymerization indicates that the transesterification and dimerization proceed simultaneously. The direct polycondensation can be used to readily produce a variety of polyesters by changing the diols under optimized conditions. Even in the presence of excess alcohols, the NHC efficiently catalyzes the dimerization through the umpolung of methacrylates combined with the activation of alcohols for transesterification.

Graphical abstract: Polycondensation of methacrylates: auto-tandem organocatalysis using N-heterocyclic carbenes

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Publication details

The article was received on 12 Jul 2018, accepted on 09 Oct 2018 and first published on 10 Oct 2018


Article type: Paper
DOI: 10.1039/C8PY01027G
Citation: Polym. Chem., 2018,9, 5295-5302
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    Polycondensation of methacrylates: auto-tandem organocatalysis using N-heterocyclic carbenes

    A. Fukumoto, M. Arimoto, S. Matsuoka and M. Suzuki, Polym. Chem., 2018, 9, 5295
    DOI: 10.1039/C8PY01027G

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