Pd(0)-Catalyzed Highly Selective Synthesis of 1,1-Diarylpropadienes and 1,3-Diarylpropynes from 1-Aryl-1-propynes and Aryl Halides

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Abstract

Under different reaction conditions, 1,1-diarylpropadienes and 1,3-diarylpropynes can be prepared respectively by the sequential lithiation of 1-aryl-1-propynes, transmetalation, and the corresponding Pd(0)-catalyzed cross-coupling with aryl halides. A rationale for the formation of 1,3-diarylpropynes is proposed.

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This article has been cited by 2 ACS Journal articles (2 most recent appear below).

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  Lewis Acid Catalyzed Propargylation of Arenes with O-Propargyl Trichloroacetimidates:  Synthesis of 1,3-Diarylpropynes

  Changkun Li and Jianbo Wang
  The Journal of Organic Chemistry2007 72 (19), 7431-7434

  • Lewis Acid Catalyzed Propargylation of Arenes with O-Propargyl Trichloroacetimidates:  Synthesis of 1,3-Diarylpropynes

    Changkun Li and Jianbo Wang
    The Journal of Organic Chemistry2007 72 (19), 7431-7434

    The BF3·OEt2-catalyzed Friedel−Crafts propargylation of aromatic compounds with O-propargyl trichloroacetimidates is highly efficient and affords 1,3-diarylpropyne derivatives in good yields.

    Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
• 

  Substitution of Hydroxyl Groups with Alkynyl Moieties Using Alkynylboron Dihalides:  An Efficient Approach to Secondary Alkylacetylene Derivatives

  George W. Kabalka, Min-Liang Yao, and Scott Borella
  Organic Letters2006 8 (5), 879-881

  • Substitution of Hydroxyl Groups with Alkynyl Moieties Using Alkynylboron Dihalides:  An Efficient Approach to Secondary Alkylacetylene Derivatives

    George W. Kabalka, Min-Liang Yao, and Scott Borella
    Organic Letters2006 8 (5), 879-881

    The reaction of alkynylboron dihalides with benzylic, allylic, and propargylic alcohols provides an efficient route to internal acetylenes. Isomerization of the product alkynes does not occur under the reaction conditions.

    Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links

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