Acid-catalyzed domino reactions of tetraarylbut-2-yne-1,4-diols. Synthesis of conjugated indenes and inden-2-ones.

J Org Chem

Centro de Quı́mica-Vila Real, Universidade de Trás-os-Montes e Alto Douro , 5000-801 Vila Real, Portugal.

Published: June 2014

AI Article Synopsis

  • The reaction of tetraarylbut-2-yne-1,4-diols with electron-rich aromatic compounds, using p-TsOH as a catalyst at room temperature, leads to the creation of substituted polycyclic aromatic indene derivatives.
  • This process involves a domino reaction that forms a cationic allenylium intermediate, which can participate in competitive intramolecular cascade reactions.
  • The described method efficiently synthesizes substituted indenes and inden-2-ones from aromatic ketones in just two steps.

Article Abstract

The reaction of tetraarylbut-2-yne-1,4-diols with electron-rich aromatic compounds at room temperature, under p-TsOH catalysis, affords substituted polycyclic aromatic indene derivatives through a domino reaction involving the formation of a cationic allenylium intermediate. This species can undergo a series of competitive intramolecular cascade reactions, leading to a conjugated inden-2-one. This simple method allows the efficient synthesis of substituted indenes and inden-2-ones, in two steps, from aromatic ketones.

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http://dx.doi.org/10.1021/jo500907zDOI Listing

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Acid-catalyzed domino reactions of tetraarylbut-2-yne-1,4-diols. Synthesis of conjugated indenes and inden-2-ones.

J Org Chem

June 2014

Centro de Quı́mica-Vila Real, Universidade de Trás-os-Montes e Alto Douro , 5000-801 Vila Real, Portugal.

Article Synopsis
  • The reaction of tetraarylbut-2-yne-1,4-diols with electron-rich aromatic compounds, using p-TsOH as a catalyst at room temperature, leads to the creation of substituted polycyclic aromatic indene derivatives.
  • This process involves a domino reaction that forms a cationic allenylium intermediate, which can participate in competitive intramolecular cascade reactions.
  • The described method efficiently synthesizes substituted indenes and inden-2-ones from aromatic ketones in just two steps.
View Article and Find Full Text PDF

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