Issue 10, 2015
From the journal:

Chemical Communications

Metal-free nitrative cyclization of N-aryl imines with tert-butyl nitrite: dehydrogenative access to 3-nitroindoles†

Guo-Bo Deng,a   Jia-Ling Zhang,a   Yan-Yun Liu,a   Bang Liu,a   Xu-Heng Yanga  and  Jin-Heng Li*a  

* Corresponding authors

a State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082, China
E-mail: jhli@hnu.edu.cn
Fax: +86 731 8871 3642
Tel: +86 731 8882 2286

Abstract

We describe here a new metal-free route for the synthesis of 3-nitroindoles by the nitrative cyclization of N-aryl imines with tert-butyl nitrite. The radical transformation allows the assembly of the indole framework through oxidative cleavage of multi C–H bonds, a nitration, cyclization and isomerization cascade.

Graphical abstract: Metal-free nitrative cyclization of N-aryl imines with tert-butyl nitrite: dehydrogenative access to 3-nitroindoles

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Article information

DOI
https://doi.org/10.1039/C4CC08498E
Article type
Communication
Submitted
28 Oct 2014
Accepted
11 Dec 2014
First published
12 Dec 2014

Chem. Commun., 2015,51, 1886-1888

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Metal-free nitrative cyclization of N-aryl imines with tert-butyl nitrite: dehydrogenative access to 3-nitroindoles

G. Deng, J. Zhang, Y. Liu, B. Liu, X. Yang and J. Li, Chem. Commun., 2015, 51, 1886 DOI: 10.1039/C4CC08498E

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