Issue 24, 2016
From the journal:

Chemical Communications

Aerobic oxidative cyclization of benzamides via meta-selective C–H tert-alkylation: rapid entry to 7-alkylated isoquinolinediones†

Shi Tang,*a   You-Lin Deng,a   Jie Li,a   Wen-Xin Wang,a   Ying-Chun Wang,a   Zeng-Zeng Li,a   Li Yuan,a   Shi-Lu Chen*b  and  Rui-Long Shengc  

* Corresponding authors

a College of Chemistry and Chemical Engineering, Jishou University, Jishou 416000, China
E-mail: stang@jsu.edu.cn

b Key Laboratory of Cluster Science of Ministry of Education, School of Chemistry, Beijing Institute of Technology, Beijing 100081, China

c Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai, China

Abstract

A novel copper-catalyzed aerobic oxidative cyclization of benzamides via meta-selective C–H tert-alkylation using AIBN and analogues as radical precursors was described. This strategy provides an elusive and rapid means to 7-tert-alkylated isoquinolinediones, as well as the construction of tertiary alkyl–aryl C(sp3)–C(sp2) bonds with positional selectivity.

Graphical abstract: Aerobic oxidative cyclization of benzamides via meta-selective C–H tert-alkylation: rapid entry to 7-alkylated isoquinolinediones

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Article information

DOI
https://doi.org/10.1039/C5CC10464E
Article type
Communication
Submitted
21 Dec 2015
Accepted
10 Feb 2016
First published
10 Feb 2016

Chem. Commun., 2016,52, 4470-4473

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Aerobic oxidative cyclization of benzamides via meta-selective C–H tert-alkylation: rapid entry to 7-alkylated isoquinolinediones

S. Tang, Y. Deng, J. Li, W. Wang, Y. Wang, Z. Li, L. Yuan, S. Chen and R. Sheng, Chem. Commun., 2016, 52, 4470 DOI: 10.1039/C5CC10464E

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