Issue 82, 2014
From the journal:

Chemical Communications

N-Heterocyclic carbene-catalyzed double acylation of enones with benzils†

Ken Takaki,*a   Akira Ohno,a   Makoto Hino,a   Takashi Shitaoka,a   Kimihiro Komeyamaa  and  Hiroto Yoshidaa  

* Corresponding authors

a Department of Applied Chemistry, Graduate School of Engineering, Hiroshima University, Kagamiyama, Higashi-Hiroshima 739-8527, Japan
E-mail: ktakaki@hiroshima-u.ac.jp

Abstract

Thiazolium carbene-catalyzed reaction of aromatic 1,2-diketones with enones in aprotic solvents gave double acylation products in good yields, whereas hydroacylation products formed by Stetter reaction were not detected at all. These results suggested the generation of aroyloxyenamine species from the 1,2-diketones instead of hydroxyenamines (Breslow intermediates).

Graphical abstract: N-Heterocyclic carbene-catalyzed double acylation of enones with benzils

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Article information

DOI
https://doi.org/10.1039/C4CC05436A
Article type
Communication
Submitted
15 Jul 2014
Accepted
26 Aug 2014
First published
26 Aug 2014

Chem. Commun., 2014,50, 12285-12288

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N-Heterocyclic carbene-catalyzed double acylation of enones with benzils

K. Takaki, A. Ohno, M. Hino, T. Shitaoka, K. Komeyama and H. Yoshida, Chem. Commun., 2014, 50, 12285 DOI: 10.1039/C4CC05436A

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