Issue 80, 2014
From the journal:

Chemical Communications

Sydnone anions and abnormal N-heterocyclic carbenes of O-ethylsydnones. Characterizations, calculations and catalyses†

Sascha Wiechmann,a   Tyll Freese,a   Martin H. H. Drafz,a   Eike G. Hübner,a   Jan C. Namyslo,a   Martin Niegerb  and  Andreas Schmidt*a  

* Corresponding authors

a Clausthal University of Technology, Institute of Organic Chemistry, Leibnizstrasse 6, D-38678 Clausthal-Zellerfeld, Germany
E-mail: schmidt@ioc.tu-clausthal.de

b Laboratory of Inorganic Chemistry, Department of Chemistry, University of Helsinki, P.O. Box 55 (A.I. Virtasen aukio 1), Helsinki, Finland

Abstract

Deprotonated sydnones, which can be represented as anionic N-heterocyclic carbenes, were prepared as Li adducts and compared with deprotonated O-ethylsydnones (5-ethoxy-1,2,3-oxadiazol-4-ylidenes) which belong to the class of abnormal NHCs. The Pd complexes of the sydnone anions (X-ray analysis) as well as of the O-ethylsydnone carbenes proved to be efficient catalysts in aryl couplings of thiophenes.

Graphical abstract: Sydnone anions and abnormal N-heterocyclic carbenes of O-ethylsydnones. Characterizations, calculations and catalyses

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Article information

DOI
https://doi.org/10.1039/C4CC05461J
Article type
Communication
Submitted
15 Jul 2014
Accepted
15 Aug 2014
First published
18 Aug 2014
This article is Open Access
Creative Commons BY license

Chem. Commun., 2014,50, 11822-11824

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Sydnone anions and abnormal N-heterocyclic carbenes of O-ethylsydnones. Characterizations, calculations and catalyses

S. Wiechmann, T. Freese, M. H. H. Drafz, E. G. Hübner, J. C. Namyslo, M. Nieger and A. Schmidt, Chem. Commun., 2014, 50, 11822 DOI: 10.1039/C4CC05461J

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