Issue 23, 2013
From the journal:

Organic & Biomolecular Chemistry

From N-benzoylpyridinium imides to pyrazolo[1,5-a]pyridines: a mechanistic discussion on a stoichiometric Cu protocol†

Lin Ling,‡b   Jingqing Chen,‡a   Jiahui Song,a   Yuhai Zhang,a   Xinqian Li,b   Lijuan Song,a   Feng Shi,*a   Yuxue Li*b  and  Chunrui Wu*a  

* Corresponding authors

a Key Laboratory of Natural Medicine and Immuno-Engineering of Henan Province, Henan University, Jinming Campus, Kaifeng, Henan 475004, P. R. China
E-mail: fshi@henu.edu.cn, cwu@henu.edu.cn
Fax: +86-378-286-4665
Tel: +86-378-286-4665

b State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Ling Ling Road, Shanghai 200032, China
E-mail: liyuxue@sioc.ac.cn

Abstract

A Cu-mediated preparation of 2-substitiuted pyrazolo[1,5-a]pyridines from N-benzoylpyridinium imides and terminal alkynes is described using stoichiometric Cu(OAc)2 as both the mediator and the oxidant. Extensive DFT calculations suggest a Cu(III) intermediate via disproportionation of Cu(II).

Graphical abstract: From N-benzoylpyridinium imides to pyrazolo[1,5-a]pyridines: a mechanistic discussion on a stoichiometric Cu protocol

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Article information

DOI
https://doi.org/10.1039/C3OB40448J
Article type
Paper
Submitted
25 Feb 2013
Accepted
04 Apr 2013
First published
09 Apr 2013

Org. Biomol. Chem., 2013,11, 3894-3902

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From N-benzoylpyridinium imides to pyrazolo[1,5-a]pyridines: a mechanistic discussion on a stoichiometric Cu protocol

L. Ling, J. Chen, J. Song, Y. Zhang, X. Li, L. Song, F. Shi, Y. Li and C. Wu, Org. Biomol. Chem., 2013, 11, 3894 DOI: 10.1039/C3OB40448J

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