Intramolecular [4 + 2] Cycloadditions of Benzynes with Conjugated Enynes, Arenynes, and Dienes

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Abstract

Benzynes generated by the reaction of o-(trimethylsilyl)aryl triflates with TBAT participate in intramolecular [4 + 2] cycloadditions with conjugated enynes, arenynes, and dienes to furnish highly condensed polycyclic aromatic compounds.

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This article has been cited by 12 ACS Journal articles (5 most recent appear below).

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  The Role of Gold Acetylides as a Selectivity Trigger and the Importance of gem-Diaurated Species in the Gold-Catalyzed Hydroarylating-Aromatization of Arene-Diynes

  A. Stephen K. Hashmi, Ingo Braun, Matthias Rudolph, and Frank Rominger
  Organometallics2012 31 (2), 644-661

  • The Role of Gold Acetylides as a Selectivity Trigger and the Importance of gem-Diaurated Species in the Gold-Catalyzed Hydroarylating-Aromatization of Arene-Diynes

    A. Stephen K. Hashmi, Ingo Braun, Matthias Rudolph, and Frank Rominger
    Organometallics2012 31 (2), 644-661

    Terminal 1,2-dialkynylarenes undergo an unexpected cyclization hydroarylation reaction toward naphthalene derivatives in benzene as the solvent. The regioselectivity of the reaction can be controlled by careful catalyst tuning. Also, the preparation of a ...

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

  Concerted vs Stepwise Mechanisms in Dehydro-Diels–Alder Reactions

  Aida Ajaz, Alexander Z. Bradley, Richard C. Burrell, William Hoi Hong Li, Kimberly J. Daoust, Laura Boddington Bovee, Kenneth J. DiRico, and Richard P. Johnson
  The Journal of Organic Chemistry2011 76 (22), 9320-9328

  • Concerted vs Stepwise Mechanisms in Dehydro-Diels–Alder Reactions

    Aida Ajaz, Alexander Z. Bradley, Richard C. Burrell, William Hoi Hong Li, Kimberly J. Daoust, Laura Boddington Bovee, Kenneth J. DiRico, and Richard P. Johnson
    The Journal of Organic Chemistry2011 76 (22), 9320-9328

    The Diels–Alder reaction is not limited to 1,3-dienes. Many cycloadditions of enynes and a smaller number of examples with 1,3-diynes have been reported. These “dehydro”-Diels–Alder cycloadditions are one class of dehydropericyclic reactions which have ...

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

  Intramolecular Aryne–Ene Reaction: Synthetic and Mechanistic Studies

  David A. Candito, Jane Panteleev, and Mark Lautens
  Journal of the American Chemical Society2011 Article ASAP

  • Intramolecular Aryne–Ene Reaction: Synthetic and Mechanistic Studies

    David A. Candito, Jane Panteleev, and Mark Lautens
    Journal of the American Chemical Society2011 Article ASAP

    Although the chemistry of arynes is well developed, some challenges still remain. The ene reaction of arynes has not gained widespread use in synthesis as a result of poor yields and selectivity. A general, high yielding and selective intramolecular aryne–...

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

  Efficient Synthesis of 2-(Trimethylsilyl)phenyl Trifluoromethanesulfonate: A Versatile Precursor to o-Benzyne

  Sarah M. Bronner and Neil K. Garg
  The Journal of Organic Chemistry2009 74 (22), 8842-8843

  • Efficient Synthesis of 2-(Trimethylsilyl)phenyl Trifluoromethanesulfonate: A Versatile Precursor to o-Benzyne

    Sarah M. Bronner and Neil K. Garg
    The Journal of Organic Chemistry2009 74 (22), 8842-8843

    An efficient procedure for the gram-scale preparation of 2-(trimethylsilyl)phenyl trifluoromethanesulfonate, a versatile precursor to o-benzyne, is presented. The three-step sequence utilizes phenol as the starting material, requires only one ...

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

  Efficient Highly Selective Synthesis of Methyl 2-(Ethynyl)alk-2(E)-enoates and 2-(1′-Chlorovinyl)alk-2(Z)-enoates from 2-(Methoxycarbonyl)-2,3-allenols

  Youqian Deng, Xin Jin, Chunling Fu and Shengming Ma
  Organic Letters2009 11 (10), 2169-2172

  • Efficient Highly Selective Synthesis of Methyl 2-(Ethynyl)alk-2(E)-enoates and 2-(1′-Chlorovinyl)alk-2(Z)-enoates from 2-(Methoxycarbonyl)-2,3-allenols

    Youqian Deng, Xin Jin, Chunling Fu and Shengming Ma
    Organic Letters2009 11 (10), 2169-2172

    Highly regio- and stereoselective reactions of readily available 2-(methoxycarbonyl)-2,3-allenols 1 with oxalyl chloride in the presence of Et3N or DMSO afforded methyl 2-(ethynyl)alk-2(E)-enoates (E)-2 and 2-(1′-chlorovinyl)alk-2(Z)-enoates (Z)-3, ...

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

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