Synlett 2023; 34(12): 1457-1461
DOI: 10.1055/a-2043-4862
cluster
Special Issue Honoring Masahiro Murakami’s Contributions to Science

Facile Synthesis of Isoindolinones via Radical-Mediated Intramolecular Coupling of Two C–H Bonds

Shuxiong Han
a   Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou 215123, P. R. of China
,
Shuo He
a   Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou 215123, P. R. of China
,
Zhibin Huang
a   Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou 215123, P. R. of China
,
Yingsheng Zhao
a   Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou 215123, P. R. of China
,
Gong Chen
b   State Key Laboratory and Institute of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin, 300071, P. R. of China
› Author Affiliations
This work was supported by National Natural Science Foundation of China (No. 22171197), the Major Basic Research Project of the Natural Science Foundation of Jiangsu Higher Education Institutions (21KJA150002), National Local Joint Engineering Laboratory to Functional Adsorption Material Technology for the Environmental Protection (SDGC2121) and the Priority Academic Program Development of Jiangsu Higher Education Institutions (PAPD) project. The project was also supported by the Open Research Fund of the School of Chemistry and Chemical Engineering, Henan Normal University.


Abstract

A metal-free method for the construction of 3,3-dimethyl isoindolinones via radical-mediated intramolecular coupling of two C–H bonds of N,N-diisopropyl benzamides was developed. The reactions can proceed in moderate to high yield and with excellent chemoselectivity. A reaction sequence of the formation of an alkyl radical via oxidative cleavage of alkyl C–H bond and the formation of lactam ring via intramolecular homolytic aromatic substitution was proposed.

Supporting Information



Publication History

Received: 15 January 2023

Accepted after revision: 27 February 2023

Accepted Manuscript online:
27 February 2023

Article published online:
17 March 2023

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