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Development and Applications of Transesterification Reactions Catalyzed by N-Heterocyclic Olefins

Marcus Blümel, Janina-Miriam Noy, Dieter Enders, Martina H. Stenzel and Thanh V. Nguyen*

*School of Chemistry, University of New South Wales, Sydney, NSW 2052, Australia, Email: t.v.nguyenunsw.edu.au

M. Blümel, J.-M. Noy, D. Enders, M. H. Stenzel, T. V. Nguyen, Org. Lett., 2016, 18, 2208-2211.

DOI: 10.1021/acs.orglett.6b00835 (free Supporting Information)


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Abstract

Catalytic amounts of alkylidene derivatives of N-heterocyclic carbenes promote transesterification reactions. Because of their strong Brĝnsted/Lewis basicity, these organocatalysts can enhance the nucleophilicity of alcohols for acylation reactions with carboxylic esters.

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proposed mechanism



Key Words

transesterifications, organocatalysis


ID: J54-Y2016