tert-Butyl peroxybenzoate (TBPB)-mediated 2-isocyanobiaryl insertion with 1,4-dioxane: efficient synthesis of 6-alkyl phenanthridines via C(sp3)–H/C(sp2)–H bond functionalization

Jia-Jia Cao; Tong-Hao Zhu; Shun-Yi Wang; Zheng-Yang Gu; Xiang Wang; Shun-Jun Ji

doi:10.1039/C4CC00743C

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tert-Butyl peroxybenzoate (TBPB)-mediated 2-isocyanobiaryl insertion with 1,4-dioxane: efficient synthesis of 6-alkyl phenanthridines via C(sp³)–H/C(sp²)–H bond functionalization†

Jia-Jia Cao,^a Tong-Hao Zhu,^a Shun-Yi Wang,*^a Zheng-Yang Gu,^a Xiang Wang^a and Shun-Jun Ji*^a

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* Corresponding authors

^a Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou 215123, China
E-mail: shunyi@suda.edu.cn, shunjun@suda.edu.cn
Fax: +86-512-65880307
Tel: +86-512-65880307

Abstract

An efficient method for the construction of 6-alkyl phenanthridines by tert-butyl peroxybenzoate (TBPB)-mediated 2-isocyanobiaryl insertion with 1,4-dioxane was established. Two new C–C bonds were formed in this reaction via a sequential C(sp³)–H/C(sp²)–H bond functionalization under metal-free conditions.

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Article information

DOI: https://doi.org/10.1039/C4CC00743C
Article type: Communication
Submitted: 28 Jan 2014
Accepted: 24 Feb 2014
First published: 24 Feb 2014

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Chem. Commun., 2014,50, 6439-6442

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tert-Butyl peroxybenzoate (TBPB)-mediated 2-isocyanobiaryl insertion with 1,4-dioxane: efficient synthesis of 6-alkyl phenanthridines via C(sp³)–H/C(sp²)–H bond functionalization

J. Cao, T. Zhu, S. Wang, Z. Gu, X. Wang and S. Ji, Chem. Commun., 2014, 50, 6439 DOI: 10.1039/C4CC00743C

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