Issue 121, 2015
From the journal:

RSC Advances

Metal-free TBHP-mediated oxidative ring openings of 2-arylimidazopyridines via regioselective cleavage of C–C and C–N bonds†

Kelu Yan,a   Daoshan Yang,*a   Wei Wei,a   Guoqing Li,a   Mingyang Sun,a   Qingyun Zhang,a   Laijin Tiana  and  Hua Wang*a  

* Corresponding authors

a The Key Laboratory of Life-Organic Analysis, Key Laboratory of Pharmaceutical Intermediates and Analysis of Natural Medicine, School of Chemistry and Chemical Engineering, Qufu Normal University, Qufu 273165, Shandong, P. R. China
E-mail: yangdaoshan@tsinghua.org.cn, huawang_qfnu@126.com

Abstract

A highly regioselective TBHP-mediated ring opening of imidazopyridines via cleavage of C–C and C–N bonds has been achieved for the first time to afford N-(pyridin-2-yl)benzamides. Preliminary mechanistic investigations revealed that the present metal-free transformation involved a radical pathway, and the oxygen atom incorporated in the end products might derive from TBHP.

Graphical abstract: Metal-free TBHP-mediated oxidative ring openings of 2-arylimidazopyridines via regioselective cleavage of C–C and C–N bonds

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Article information

DOI
https://doi.org/10.1039/C5RA17740E
Article type
Communication
Submitted
20 Oct 2015
Accepted
16 Nov 2015
First published
17 Nov 2015

RSC Adv., 2015,5, 100102-100105

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Metal-free TBHP-mediated oxidative ring openings of 2-arylimidazopyridines via regioselective cleavage of C–C and C–N bonds

K. Yan, D. Yang, W. Wei, G. Li, M. Sun, Q. Zhang, L. Tian and H. Wang, RSC Adv., 2015, 5, 100102 DOI: 10.1039/C5RA17740E

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