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Chinese Journal of Organic Chemistry >

2019 , Vol. 39 >Issue 6: 1665 - 1671

DOI: https://doi.org/10.6023/cjoc201903037

Articles

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

  • Zhu Ye ,
  • Huang Jinwen ,
  • Yang Xianjin
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  • 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 date: 2019-03-20

  Revised date: 2019-04-25

  Online published: 2019-05-10

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).

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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

Cite this article

Zhu Ye , Huang Jinwen , Yang Xianjin . Chlorination of Anilide by Pd(OAc)2/N-Chloro-N-fluorobenzene- sulfonylamide[J]. Chinese Journal of Organic Chemistry, 2019 , 39(6) : 1665 -1671 . DOI: 10.6023/cjoc201903037

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