CuBr-Promoted Tandem Cyclization/Trifluoromethylation of 2-Alkynylanilines: Efficient Synthesis of 3-Trifluoromethylindoles

Authors

  • Guangcun Ge,

    1. State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China
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  • Xiaojun Huang,

    1. State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China
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  • Changhua Ding,

    1. State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China
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  • Hao Li,

    1. State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China
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  • Shili Wan,

    1. State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China
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  • Xuelong Hou

    Corresponding author
    1. State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China
    2. Shanghai-Hong Kong Joint Laboratory in Chemical Synthesis, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China
    • State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China, Tel.: 0086-021-54925144

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Abstract

A new efficient strategy for the synthesis of 3-trifluoromethyl-indoles was developed through tandem cyclization/trifluoromethylation of 2-alkynylanilines and Umemoto's reagent under effect of CuBr. The reaction features the use of cheap copper salt, mild reaction conditions and high yield of products. The preliminary mechanism study indicates the solvent dimethylacetamide acts as the role of dealkylation.

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