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Indium(III)-Catalyzed Knoevenagel Condensation of Aldehydes and Activated Methylenes Using Acetic Anhydride as a Promoter

Author:
Ogiwara, Yohei, Takahashi, Keita, Kitazawa, Takefumi, Sakai, Norio
Source:
Journal of organic chemistry 2015 v.80 no.6 pp. 3101-3110
ISSN:
1520-6904
Subject:
acetic anhydride, aldehydes, catalysts, condensation reactions, heterocyclic compounds, indium, organic chemistry
Abstract:
The combination of a catalytic amount of InCl₃ and acetic anhydride remarkably promotes the Knoevenagel condensation of a variety of aldehydes and activated methylene compounds. This catalytic system accommodates aromatic aldehydes containing a variety of electron-donating and -withdrawing groups, heteroaromatic aldehydes, conjugate aldehydes, and aliphatic aldehydes. Central to successfully driving the condensation series is the formation of a geminal diacetate intermediate, which was generated in situ from an aldehyde and an acid anhydride with the assistance of an indium catalyst.
Agid:
5505209