4.5 Article

Nickel-Catalyzed 1,1-Difluoroethylation of (Hetero)aryl Halides with 1,1-Difluoroethyl Chloride (CH3CF2Cl)

Journal

ASIAN JOURNAL OF ORGANIC CHEMISTRY
Volume 9, Issue 3, Pages 391-394

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/ajoc.202000004

Keywords

1; 1-difluoroethylation; nickel; cross-coupling; aryl halides; 1; 1-difluoroethyl chloride

Funding

  1. Natural Science Foundation of Shandong Province [ZR2017BB052]
  2. Doctoral Scientific Research Foundation of Shandong University of Technology [4041-416021]
  3. open project foundation of Key Laboratory of Organofluorine Chemistry, Chinese Academy of Sciences

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1,1-Difluoroethylated aromatic compounds are of increasing importance in agrochemicals and pharmaceuticals. The direct introduction of difluoroethyl (CF2CH3) group(s) onto aromatic rings using CH3CF2Cl, an inexpensive and available raw material, still remains a great challenge because of the relatively inert C-Cl bond of CH3CF2Cl. Herein, we disclose a nickel-catalyzed 1,1-difluoroethylation of (hetero)aryl halides with CH3CF2Cl. The reaction exhibits good functional-group tolerance and is regarded as a practical method for synthesis of (1,1-difluoroethyl)arenes.

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