Get access

Silver Triflate Catalyzed Tandem Heterocyclization/Alkynylation of 1-((2-Tosylamino)aryl)but-2-yne-1,4-diols to 2-Alkynyl Indoles

Authors

  • Srinivasa Reddy Mothe,

    1. Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637371 (Singapore), Fax: (+65) 6791-1961
    Search for more papers by this author
  • Dr. Prasath Kothandaraman,

    1. Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637371 (Singapore), Fax: (+65) 6791-1961
    Search for more papers by this author
  • Sherman Jun Liang Lauw,

    1. Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637371 (Singapore), Fax: (+65) 6791-1961
    Search for more papers by this author
  • Samuel Ming Wei Chin,

    1. Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637371 (Singapore), Fax: (+65) 6791-1961
    Search for more papers by this author
  • Prof. Dr. Philip Wai Hong Chan

    Corresponding author
    1. Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637371 (Singapore), Fax: (+65) 6791-1961
    • Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637371 (Singapore), Fax: (+65) 6791-1961
    Search for more papers by this author

Abstract

original image

Don't cross me! 2-Alkynyl indoles were prepared efficiently by the AgOTf-catalyzed tandem heterocyclization/alkynylation of 1-(2-tosylamino)aryl)but-2-yne-1,4-diols under mild conditions (see scheme). The attractiveness of this approach lies in the fact that both the indole ring and alkyne side chain of the N-heterocycle are sequentially formed from low cost, readily available, and ecologically benign starting materials. It also provides the first route to this synthetically valuable class of compounds that is not based on a cross-coupling strategy.

Get access to the full text of this article

Ancillary