Synthesis of functionalized benzoxazines by copper-catalyzed C(sp3)–H bond functionalization of acetonitrile with olefinic amides

Xue-Qiang Chu; Xiao-Ping Xu; Hua Meng; Shun-Jun Ji

doi:10.1039/C5RA14729H

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Synthesis of functionalized benzoxazines by copper-catalyzed C(sp³)–H bond functionalization of acetonitrile with olefinic amides†

Xue-Qiang Chu,^a Xiao-Ping Xu,*^a Hua Meng^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, Collaborative Innovation Center of Suzhou Nano Science and Technology, Soochow University, Suzhou, China
E-mail: xuxp@suda.edu.cn, shunjun@suda.edu.cn
Fax: +86-512-65880307
Tel: +86-512-65880307

Abstract

A copper-mediated oxycyanomethylation reaction of olefinic amides with acetonitrile was developed for the synthesis of important benzoxazine derivatives. The reactions involve the activation of the C(sp³)–H bond of acetonitrile and radical cyclization processes for the construction of new C–C and C–O bonds.

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Article information

DOI: https://doi.org/10.1039/C5RA14729H
Article type: Communication
Submitted: 14 Jul 2015
Accepted: 30 Jul 2015
First published: 03 Aug 2015

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RSC Adv., 2015,5, 67829-67832

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Synthesis of functionalized benzoxazines by copper-catalyzed C(sp³)–H bond functionalization of acetonitrile with olefinic amides

X. Chu, X. Xu, H. Meng and S. Ji, RSC Adv., 2015, 5, 67829 DOI: 10.1039/C5RA14729H

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