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Copper-Catalyzed Coupling Reaction of C-OMe Bonds Adjacent to a Nitrogen Atom with Terminal Alkynes

  作者 YAO BANGBEN; ZHANG YUHONG; LI YONG  
  选自 期刊  Journal of Organic Chemistry;  卷期  2010年75-13;  页码  4554-4561  
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[摘要]The cross coupling of the C-OMe bond adjacent to a nitrogen atom in dialkoxy-N,N-dialkylmethanamines with terminal alkynes was efficiently approached in the presence of copper catalyst under mild conditions to give 3-amino-1,4-diynes in good yields. The reaction is promoted by phosphine ligands and the chemistry provides a simple and efficient route to 3-amino-1,4-diynes. Importantly, the Michael addition occurred with as-prepared 3-amino-1,4-diynes to give the useful Michael-adducts containing tert-alkylamines in a very convenient way. Further studies revealed that (E)-1,5-diarylpent-1-en-4-yn-3-one was formed through the rearrangement by using the neutral alumina column, and the corresponding imine 2-(1,5-diphenylpent-2-en-4-ynylideneamino)ethanol was obtained in the presence of AgOTf.

 
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