One-step construction of molecular complexity by tert-butyl nitrite (TBN)-initiated cascade α,β-sp3 C–H bond difunctionalization and C–N bond cleavage

Kaixuan He; Pengfei Li; Shuwei Zhang; Qian Chen; Honghe Ji; Yu Yuan; Xiaodong Jia

doi:10.1039/C8CC06946H

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One-step construction of molecular complexity by tert-butyl nitrite (TBN)-initiated cascade α,β-sp³ C–H bond difunctionalization and C–N bond cleavage†

Kaixuan He,^a Pengfei Li,^b Shuwei Zhang,^a Qian Chen,^a Honghe Ji,^b Yu Yuan^a and Xiaodong Jia

*^a

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* Corresponding authors

^a School of Chemistry & Chemical Engineering, Yangzhou University, Siwangting Road 180, Yangzhou, Jiangsu 225002, China
E-mail: jiaxd1975@163.com

^b College of Chemistry & Chemical Engineering, Northwest Normal University, Anning East Road 967, Lanzhou, Gansu 730070, China

Abstract

TBN-initiated cascade multifunctionalization of inert C–H and C–N bonds in N-arylazacycles has been realized under transition-metal free conditions, in which the synthetically useful oxime, N–NO and aldehyde functional groups were constructed in only one synthetic step.

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Article information

DOI: https://doi.org/10.1039/C8CC06946H
Article type: Communication
Submitted: 05 Sep 2018
Accepted: 25 Oct 2018
First published: 26 Oct 2018

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Chem. Commun., 2018,54, 13232-13235

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One-step construction of molecular complexity by tert-butyl nitrite (TBN)-initiated cascade α,β-sp³ C–H bond difunctionalization and C–N bond cleavage

K. He, P. Li, S. Zhang, Q. Chen, H. Ji, Y. Yuan and X. Jia, Chem. Commun., 2018, 54, 13232 DOI: 10.1039/C8CC06946H

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Chemical Communications