Regioselective synthesis of isoquinolinonediones through remote unactivated C(sp3)–H bonds

Lei Huang; Jun Sun; Boxuan Sun; Shengjie Song; Jianjun Li

doi:10.1039/D4CC00916A

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Regioselective synthesis of isoquinolinonediones through remote unactivated C(sp³)–H bonds†

Lei Huang,^a Jun Sun,^a Boxuan Sun,^a Shengjie Song^a and Jianjun Li

*^abc

Author affiliations

* Corresponding authors

^a Key Laboratory for Green Pharmaceutical Technologies and Related Equipment of Ministry of Education, College of Pharmaceutical Sciences, Zhejiang University of Technology, Hangzhou 310014, P. R. China
E-mail: lijianjun@zjut.edu.cn

^b Key Laboratory of Pharmaceutical Engineering of Zhejiang Province, College of Pharmaceutical Sciences, Zhejiang University of Technology, Hangzhou 310014, P. R. China

^c Taizhou Key Laboratory of Advanced Manufacturing Technology, Taizhou Institute, Zhejiang University of Technology, Taizhou 318014, P. R. China

Abstract

Herein, a general strategy for the remote-site-selective cascade addition/cyclization of unactivated C(sp³)–H bonds in free alcohols and sulfonamides to build isoquinolinonedione skeletons is developed. The site selectivity occurs predominantly via a 1,5-hydrogen atom transfer (HAT) process, triggered by heteroatom-centred radicals generated directly under silver catalysis. A broad substrate scope and excellent regio-/chemo-selective control are demonstrated in this method.

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Article information

DOI: https://doi.org/10.1039/D4CC00916A
Article type: Communication
Submitted: 26 Feb 2024
Accepted: 02 Apr 2024
First published: 02 Apr 2024

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Chem. Commun., 2024,60, 4818-4821

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Regioselective synthesis of isoquinolinonediones through remote unactivated C(sp³)–H bonds

L. Huang, J. Sun, B. Sun, S. Song and J. Li, Chem. Commun., 2024, 60, 4818 DOI: 10.1039/D4CC00916A

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