4.7 Article

Synthetic Access to Secondary Propargylamines via a Copper-Catalyzed Oxidative Deamination/Alkynylation Cascade

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 84, Issue 16, Pages 10501-10508

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.9b01431

Keywords

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Funding

  1. Innovation Research Projects of Shanghai University of Engineering Science [201810856017, cs1704006, A1-0601-19-01017]
  2. Opening Project of Shanghai Key Laboratory of Chemical Biology
  3. RUDN University Program 5-100

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A novel and selective cascade reaction of primary amines and alkynes for the synthesis of the corresponding secondary propargylamines is described. This protocol proceeds with a CuBr2/TBHP system through a process of oxidative deamination of primary amines to imine and alkynylation, featuring a wide scope of substrates with good functional-group tolerance and operational simplicity. Additionally, the use of two different primary amines could also work smoothly using this protocol.

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