Visible-Light Promoted Hydroxylation of Aryl Halides under Mild Reaction Conditions in Neat Water

doi:10.6023/cjoc202005004

Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (9): 2912-2918.DOI: 10.6023/cjoc202005004 Previous Articles Next Articles

Special Issue: 有机光催化虚拟合辑

水相中可见光催化卤代芳烃羟基化反应

许秀枝^a, 张帆^b, 黄胜^a, 张志强^a, 柯方^a

a 福建医科大学药学院福建省天然药物药理学重点实验室福州 350004;
b 福建医科大学附属第一医院肿瘤内科福州 350005

收稿日期:2020-05-02 修回日期:2020-06-12 发布日期:2020-07-17
通讯作者: 许秀枝, 柯方 E-mail:xiuzhi_xu@126.com;kefang612@163.com
基金资助:
福建省自然科学基金（Nos.2016Y9052，2016Y9053，2017J01820，2017-1-64）资助项目.

Visible-Light Promoted Hydroxylation of Aryl Halides under Mild Reaction Conditions in Neat Water

Xu Xiuzhi^a, Zhang Fan^b, Huang Sheng^a, Zhang Zhiqiang^a, Ke Fang^a

a Fujian Provincial Key Laboratory of Natural Medicine Pharmacolog, Department of Pharmacy, Fujian Medical University, Fuzhou 350004;
b The First Affiliated Hospital of Fujian Medical University Oncology, Fuzhou 35000

Received:2020-05-02 Revised:2020-06-12 Published:2020-07-17
Supported by:
Project supported by the Natural Science Foundation of Fujian Province (Nos. 2016Y9052, 2016Y9053, 2017J01820, 2017-1-64).

1. cjoc202005004.pdf(1096KB)

Abstract

A novel visible-light-introduced reaction for the construction of phenols via hydroxylation of aryl halides has been developed. The reaction has been achieved in high yield under mild conditions by using iodine as photocatalyst, which is cheap, easy to handle and environmentally friendly. A variety of phenols were obtained in up to 92% yields. Moreover, aryl chlorides were also successfully employed as substrates, affording the target phenols in good isolated yields. It might provide promising protocol for the synthesis of phenol derivatives. Its application was performed by the synthesis of 5-acetyl-4-hy-droxy-2-methoxybenzyl diisopropylcarbamodithioate, which displayed significant anti-proliferation effect.

Key words: visible-light promoted, iodine, aryl halides, hydroxylation

Cite this article

Xu Xiuzhi, Zhang Fan, Huang Sheng, Zhang Zhiqiang, Ke Fang. Visible-Light Promoted Hydroxylation of Aryl Halides under Mild Reaction Conditions in Neat Water[J]. Chinese Journal of Organic Chemistry, 2020, 40(9): 2912-2918.

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水相中可见光催化卤代芳烃羟基化反应

Visible-Light Promoted Hydroxylation of Aryl Halides under Mild Reaction Conditions in Neat Water

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