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Communication
Silver Triflate Catalyzed Tandem Heterocyclization/Alkynylation of 1-((2-Tosylamino)aryl)but-2-yne-1,4-diols to 2-Alkynyl Indoles
Article first published online: 18 APR 2012
DOI: 10.1002/chem.201200578
Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Additional Information
How to Cite
Mothe, S. R., Kothandaraman, P., Lauw, S. J. L., Chin, S. M. W. and Chan, P. W. H. (2012), Silver Triflate Catalyzed Tandem Heterocyclization/Alkynylation of 1-((2-Tosylamino)aryl)but-2-yne-1,4-diols to 2-Alkynyl Indoles. Chem. Eur. J., 18: 6133–6137. doi: 10.1002/chem.201200578
Publication History
- Issue published online: 3 MAY 2012
- Article first published online: 18 APR 2012
- Manuscript Received: 22 FEB 2012
Funded by
- University Research Committee Grant. Grant Number: RG55/06
- Nanyang Technological University
- Science and Engineering Research Council. Grant Number: 092 101 0053
- NTU
Keywords:
- alcohols;
- heterocyclization/alkynylation;
- homogeneous catalysis;
- indoles;
- silver
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.