Iridium(III)-Catalyzed Approach for the Synthesis of Fused Arenes: Access to Isoindolines, Indanes, and Dihydroisobenzofurans

Authors

  • Dr. Anne-Laure Auvinet,

    1. ENSCP Chimie ParisTech Laboratoire Charles Friedel, 11 rue P. et M. Curie, 75005 Paris (France), Fax: (+33) 144071062
    2. CNRS, UMR 7223, 75005 Paris (France)
    Search for more papers by this author
  • Dr. Mehdi Ez-Zoubir,

    1. ENSCP Chimie ParisTech Laboratoire Charles Friedel, 11 rue P. et M. Curie, 75005 Paris (France), Fax: (+33) 144071062
    2. CNRS, UMR 7223, 75005 Paris (France)
    Search for more papers by this author
  • Savinien Bompard,

    1. ENSCP Chimie ParisTech Laboratoire Charles Friedel, 11 rue P. et M. Curie, 75005 Paris (France), Fax: (+33) 144071062
    2. CNRS, UMR 7223, 75005 Paris (France)
    Search for more papers by this author
  • Dr. Maxime R. Vitale,

    1. ENSCP Chimie ParisTech Laboratoire Charles Friedel, 11 rue P. et M. Curie, 75005 Paris (France), Fax: (+33) 144071062
    2. CNRS, UMR 7223, 75005 Paris (France)
    Search for more papers by this author
  • Jack A. Brown,

    1. GlaxoSmithKline, Medicines Research Centre, Gunnels Wood Road, Stevenage, SG1 2NY (UK)
    Search for more papers by this author
  • Dr. Véronique Michelet,

    Corresponding author
    1. ENSCP Chimie ParisTech Laboratoire Charles Friedel, 11 rue P. et M. Curie, 75005 Paris (France), Fax: (+33) 144071062
    2. CNRS, UMR 7223, 75005 Paris (France)
    • ENSCP Chimie ParisTech Laboratoire Charles Friedel, 11 rue P. et M. Curie, 75005 Paris (France), Fax: (+33) 144071062
    Search for more papers by this author
  • Dr. Virginie Ratovelomanana-Vidal

    Corresponding author
    1. ENSCP Chimie ParisTech Laboratoire Charles Friedel, 11 rue P. et M. Curie, 75005 Paris (France), Fax: (+33) 144071062
    2. CNRS, UMR 7223, 75005 Paris (France)
    • ENSCP Chimie ParisTech Laboratoire Charles Friedel, 11 rue P. et M. Curie, 75005 Paris (France), Fax: (+33) 144071062
    Search for more papers by this author

Abstract

A facile and efficient method for the synthesis of isoindoline, indane, and dihydroisobenzofuran derivatives has been developed through the application of a halogen-bridged iridium(III) complex to the [2+2+2] cycloaddition of α,ω-diynes with alkynes. The cycloaddition tolerates a broad range of substitution groups, such as alcohol, alkyl, ether, and halogen, and the chemistry can be extended to prepare the corresponding borylated fused arenes. The reaction shows that hindered starting materials are also good partners, which provide the desired fused arenes in good yields.

Ancillary