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; Zhixia Zhuang

doi:10.1021/acs.orglett.7b02442

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

Org Lett. 2017 Oct 6;19(19):5170-5173. doi: 10.1021/acs.orglett.7b02442. Epub 2017 Sep 12.

Authors

Jinhai Shen¹, Qihua You¹, Qi Fu¹, Changsheng Kuai², Huabin Huang¹, Li Zhao¹, Zhixia Zhuang¹

Affiliations

¹ Department of Science and Technology for Inspection, Xiamen Huaxia University , Xiamen 361024, China.
² School of Biomedical Sciences, Huaqiao University , Xiamen 361021, China.

PMID: 28898096
DOI: 10.1021/acs.orglett.7b02442

Abstract

A base-promoted cascade reaction for the regiospecific synthesis of substituted 3-hydroxyisoindolinones under transition-metal-free conditions is developed. The base-mediated C-C bond coupling and N-α-sp³C-H bond hydroxylation are involved in this procedure, which features high regioselectivity, efficiency, and environmental friendliness. Various substituted 3-hydroxyisoindolinones, including some bioactive molecules, were provided in up to 93% yield for 28 examples.

Publication types

Research Support, Non-U.S. Gov't