Epoxide as precatalyst for metal-free catalytic transesterification

[Display omitted] •Transesterification catalyzed by simple alkylammonium salt and epoxide.•Various esters were synthesized from abundant methyl esters.•Ring-opening reaction of epoxide generates catalytically active base catalyst. Transesterification of methyl esters was accelerated by an in situ-ge...

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Published inTetrahedron letters Vol. 60; no. 30; pp. 2009 - 2013
Main Authors Tanaka, Shinji, Nakashima, Takuya, Satou, Naoto, Oono, Hiromi, Kon, Yoshihiro, Tamura, Masanori, Sato, Kazuhiko
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 25.07.2019
Elsevier
Subjects
Ammonium salt
Chemistry
Chemistry, Organic
Epoxide
Metal-free catalyst
Physical Sciences
Science & Technology
Transesterification
Metal-free catalyst
Ammonium salt
Transesterification
Epoxide
PHOSPHONIUM SALTS
N-HETEROCYCLIC CARBENES
CYCLIC CARBONATES
IONIC LIQUIDS
EFFICIENT
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Summary:[Display omitted] •Transesterification catalyzed by simple alkylammonium salt and epoxide.•Various esters were synthesized from abundant methyl esters.•Ring-opening reaction of epoxide generates catalytically active base catalyst. Transesterification of methyl esters was accelerated by an in situ-generated metal-free catalyst comprising a quaternary alkylammonium salt and an epoxide. The combination of a quaternary alkylammonium acetate and glycidol is optimal, and various esters were synthesized from methyl esters with alcohols in good to excellent yield. Analysis of the catalyst solution revealed that basic species are generated by the ring-opening reaction of epoxide.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2019.06.056