4.7 Article

Cu(I)-Catalyzed gem-Aminoalkynylation of Diazo Compounds: Synthesis of Fluorinated Propargylic Amines

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 86, Issue 15, Pages 10928-10938

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.1c01423

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Funding

  1. Swiss National Science Foundation [200020_182798]
  2. Swiss National Science Foundation

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The gem-aminoalkynylation of fluorinated diazo compounds catalyzed by Cu(I) salt allows the synthesis of propargylic amines with broad functional group tolerance. Both electron-rich and electron-poor anilines can be used as nucleophiles, while alkyl-, aryl-, and silyl-substituted EthynylBenziodoXoles (EBX) can serve as electrophiles in this three-component reaction.
The gem-aminoalkynylation of fluorinated diazo compounds catalyzed by a simple Cu(I) salt is described. This three-component reaction allows the synthesis of propargylic amines with broad functional group tolerance. Both electron-rich and electron-poor anilines can be used as nucleophiles and alkyl-, aryl-, and silyl-substituted EthynylBenziodoXoles (EBX) as electrophiles.

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