Advertisement

Consecutive C[BOND]H Functionalization Reactions of Arenes: Synthesis of Carbo- and Heteropolycyclic Skeletons

Authors

  • Samuel Suárez-Pantiga,

    1. Departamento de Química Orgánica e Inorgánica and Instituto Universitario de Química Organometálica “Enrique Moles”-Unidad Asociada al C.S.I.C.—Universidad de Oviedo, C/Julián Clavería 8, 33006 Oviedo (Spain), Fax: (+34) 985-103-450
    Search for more papers by this author
  • David Palomas,

    1. Departamento de Química Orgánica e Inorgánica and Instituto Universitario de Química Organometálica “Enrique Moles”-Unidad Asociada al C.S.I.C.—Universidad de Oviedo, C/Julián Clavería 8, 33006 Oviedo (Spain), Fax: (+34) 985-103-450
    Search for more papers by this author
  • Eduardo Rubio Dr.,

    1. Departamento de Química Orgánica e Inorgánica and Instituto Universitario de Química Organometálica “Enrique Moles”-Unidad Asociada al C.S.I.C.—Universidad de Oviedo, C/Julián Clavería 8, 33006 Oviedo (Spain), Fax: (+34) 985-103-450
    Search for more papers by this author
  • José M. González Prof. Dr.

    1. Departamento de Química Orgánica e Inorgánica and Instituto Universitario de Química Organometálica “Enrique Moles”-Unidad Asociada al C.S.I.C.—Universidad de Oviedo, C/Julián Clavería 8, 33006 Oviedo (Spain), Fax: (+34) 985-103-450
    Search for more papers by this author

  • Financial support for this work is acknowledged (grant nos. CTQ2007-61048 and IB08-088). S.S.-P. and D.P. thank the MICINN for predoctoral FPU fellowships. We also thank Dr. Ángel L. Suárez-Sobrino for his helpful assistance with the X-ray analysis. We are grateful to the referees for their kind and helpful suggestions to improve the manuscript, particularly for the labeling experiments.

Abstract

original image

Doubling the bet: Two C[BOND]H bonds become functionalized upon exposure of ω-aryl propargylic tosylates to Sc(OTf)3 (see scheme). The reaction involves a new domino process that can tolerate both electron-withdrawing and -donating substituents on the arene unit. Different carbo- and heterocyclic frameworks can be assembled by using this approach to formally conquer the hydroarylation process.

Ancillary