title: Silver triflate catalyzed tandem heterocyclization/alkynylation of 1-((2-tosylamino)aryl)but-2-yne-1,4-diols to 2-alkynyl indoles.
abstract: 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.
authors.affiliation: Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637371, Singapore.
authors.forename: Srinivasa Reddy
authors.initials: SR
authors.lastname: Mothe
authors.forename: Prasath
authors.initials: P
authors.lastname: Kothandaraman
authors.forename: Sherman Jun Liang
authors.initials: SJ
authors.lastname: Lauw
authors.forename: Samuel Ming Wei
authors.initials: SM
authors.lastname: Chin
authors.forename: Philip Wai Hong
authors.initials: PW
authors.lastname: Chan
mesh_terms: D000438:Alcohols / Q000737:chemistry*; D000480:Alkynes / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D008698:Mesylates / Q000737:chemistry*; D015394:Molecular Structure
chemical_list: D000438:Alcohols; D000480:Alkynes; D007211:Indoles; D008698:Mesylates; C012077:trifluoromethanesulfonic acid