Chlorination of Anilide by Pd(OAc)2/N-Chloro-N-fluorobenzene- sulfonylamide

doi:10.6023/cjoc201903037

Chin. J. Org. Chem. ›› 2019, Vol. 39 ›› Issue (6): 1665-1671.DOI: 10.6023/cjoc201903037 Previous Articles Next Articles

Special Issue: 金属有机化学；碳氢活化合辑2018-2019

Articles

Pd(OAc)₂/N-氯-N-氟苯磺酰胺体系下乙酰苯胺的氯化反应

朱晔^a, 黄金文^b, 杨先金^a,c

a 华东理工大学精细化工研究所结构可控先进功能材料及其制备教育部重点实验室上海 200237;
b 上海应用技术大学化学与环境工程学院上海 201418;
c 中国科学院上海有机化学研究所有机氟化学重点实验室上海 200032

收稿日期:2019-03-20 修回日期:2019-04-25 发布日期:2019-05-10
通讯作者: 黄金文, 杨先金 E-mail:yxj@ecust.edu.cn;goldven@sit.edu.cn
基金资助:
国家自然科学基金（No.21372077）和低品位磷矿高效利用国家重点实验室（No.WFKF2017-04）资助项目.

Chlorination of Anilide by Pd(OAc)₂/N-Chloro-N-fluorobenzene- sulfonylamide

Zhu Ye^a, Huang Jinwen^b, Yang Xianjin^a,c

a Key Laboratory for Advanced Materials & Institute of Fine Chemicals, East China University of Science and Technology, Shanghai 200237;
b School of Chemical and Environmental Engineering, Shanghai Institute of Technology, Shanghai 201418;
c Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Science, Shanghai 200032

Received:2019-03-20 Revised:2019-04-25 Published:2019-05-10
Contact: 10.6023/cjoc201903037 E-mail:yxj@ecust.edu.cn;goldven@sit.edu.cn
Supported by:
Project supported by the National Natural Science Foundation of China (No. 21372077) and the State Key Laboratory of Efficient Utilization for Low Grade Phosphate Rock and Its Associated Resources (No. WFKF2017-04).

1. Chlorination of Anilide by Pd(OAc)₂/N-Chloro-N-fluorobenzene- sulfonylamide.PDF(1817KB)

Abstract

A mild method for palladium-catalyzed halogenation of acetanilide with N-chloro-N-fluorobenzenesulfonylamide (CFBSA) as a chlorinating reagent, oxidant, and novel promoting reagent was achieved. The decomposition of byproduct N-fluoroben-zenesulfonylamine in the presence of Pd(OAc)₂ could accelerate the process of chlorination. Preliminary mechanism investigation showed that Pd catalyzed anilide directed C-H activation lead to the ortho chlorination selectivity. A series of ortho-chlorinated anilides were obtained in 28%~82% yields.

Key words: chlorinating reagent, fluorine atom, Pd-catalyzed, synthetic methodology

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Zhu Ye, Huang Jinwen, Yang Xianjin. Chlorination of Anilide by Pd(OAc)₂/N-Chloro-N-fluorobenzene- sulfonylamide[J]. Chin. J. Org. Chem., 2019, 39(6): 1665-1671.

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Pd(OAc)₂/N-氯-N-氟苯磺酰胺体系下乙酰苯胺的氯化反应

Chlorination of Anilide by Pd(OAc)₂/N-Chloro-N-fluorobenzene- sulfonylamide

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Pd(OAc)2/N-氯-N-氟苯磺酰胺体系下乙酰苯胺的氯化反应