Base-Promoted Cascade C-C Coupling/N-α-sp³C-H Hydroxylation for the Regiospecific Synthesis of 3-Hydroxyisoindolinones

Jinhai Shen*, Qihua You, Qi Fu, Changsheng Kuai, Huabin Huang, Li Zhao and Zhixia Zhuang

*Department of Science and Technology for Inspection, Xiamen Huaxia University, Xiamen 361024, China, Email: shenjhhxxy.edu.cn

J. Shen, Q. You, Q. Fu, C. Kuai, H. Huang, L. Zhao, Z. Zhuang, Org. Lett., 2017, 19, 5170-5173.

DOI: 10.1021/acs.orglett.7b02442

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Abstract

A cascade reaction enables a regiospecific synthesis of substituted 3-hydroxyisoindolinones under transition-metal-free conditions via base-mediated C-C bond coupling and N-α-sp³C-H bond hydroxylation. The procedure offers high regioselectivity, efficiency, and environmental friendliness. Various substituted 3-hydroxyisoindolinones, including some bioactive molecules, were provided in very good yields.

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proposed mechanism

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Key Words

isoindolinones, oxygen

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ID: J54-Y2017