Electrochemical 5-exo-dig aza-cyclization of 2-alkynylbenzamides toward 3-hydroxyisoindolinone derivatives
Zhaojiang Shi1, Nan Li1, Wei-Zhen Wang1
1Institute of Pharmaceutical Science and Technology, College of Chemistry, Fuzhou University, Fuzhou 350108, China. yaofeng_yuan@fzu.edu.cn.
Abstract:
Preparation of biologically relevant 3-hydroxyisoindolinones from readily available 2-alkynylbenzamides is an appealing synthetic approach. However, such kinds of compounds preferably undergo O-attacked 5-exo-dig/6-endo-dig cyclizations. Herein, we report an electrochemically generated amidyl radical proceeding via a highly selective N-attacked 5-exo-dig radical cyclization to form 3-hydroxyisoindolinone derivatives. This reaction features simple operation, good selectivity, and broad substrate scope. Moreover, gram-scale preparation and synthetic elaborations imply the potential applicability of this protocol for the synthesis of diverse isoindolinone derivatives.
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