Nickel-Catalyzed Intramolecular Addition of Aryl Bromides to C=O Bonds

doi:10.6023/cjoc201610009

Chin. J. Org. Chem. ›› 2017, Vol. 37 ›› Issue (3): 652-657.DOI: 10.6023/cjoc201610009 Previous Articles Next Articles

ARTICLE

镍催化芳基溴化物对羰基的分子内加成反应

张鸣頔, 刘人荣, 高建荣, 贾义霞

浙江工业大学化学工程学院杭州 310014

收稿日期:2016-10-08 修回日期:2016-11-29 发布日期:2016-12-02
通讯作者: 贾义霞,E-mail:yxjia@zjut.edu.cn E-mail:yxjia@zjut.edu.cn
基金资助:
国家自然科学基金（Nos.21372202，21522207）资助项目.

Nickel-Catalyzed Intramolecular Addition of Aryl Bromides to C=O Bonds

Zhang Mingdi, Liu Renrong, Gao Jianrong, Jia Yixia

College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014

Received:2016-10-08 Revised:2016-11-29 Published:2016-12-02
Contact: 10.6023/cjoc201610009 E-mail:yxjia@zjut.edu.cn
Supported by:
Project supported by the National Natural Science Foundation of China (Nos. 21372202, 21522207).

1. Nickel-Catalyzed Intramolecular Addition of Aryl Bromides to C=O Bonds.PDF(1467KB)

Abstract

A nickel-catalyzed intramolecular Grignard-type addition of aryl bromides to C=O was developed. By using Ni(dppe)Br₂ as a catalyst and zinc powder as a reducing agent, the reactions of 2-((2-bromophenyl)amino)-1-arylethanones proceeded smoothly in 1,2-dimethoxyethane solvent to afford 3-hydroxyindolines as intermediates, which underwent dehydration reaction to furnish a range of indole derivatives in moderate to excellent yields (up to 90%).

Key words: nickel, addition reaction, aryl bromide, dehydration reaction, indole

Cite this article

Zhang Mingdi, Liu Renrong, Gao Jianrong, Jia Yixia. Nickel-Catalyzed Intramolecular Addition of Aryl Bromides to C=O Bonds[J]. Chin. J. Org. Chem., 2017, 37(3): 652-657.

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镍催化芳基溴化物对羰基的分子内加成反应

Nickel-Catalyzed Intramolecular Addition of Aryl Bromides to C=O Bonds

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