Silver triflate catalyzed tandem heterocyclization/alkynylation of 1-((2-tosylamino)aryl)but-2-yne-1,4-diols to 2-alkynyl indoles

• Main Authors: Mothe, Srinivasa Reddy, Kothandaraman, Prasath, Lauw, Sherman Jun Liang, Chin, Samuel Ming Wei, Chan, Philip Wai Hong
• Other Authors: School of Physical and Mathematical Sciences
• Format: Article
• Language: English
• Published: 2013
• Online Access: https://hdl.handle.net/10356/99426; http://hdl.handle.net/10220/12940
• Institution: Nanyang Technological University

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.