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The Benzyne Fischer-Indole Reaction

Donald McAusland, Sangwon Seo, Didier G. Pintori, Jonathan Finlayson and Michael F. Greaney*

*University of Edinburgh, School of Chemistry, Joseph Black Building, King’s Buildings, West Mains Road, Edinburgh, EH9 3JJ, U.K., Email: michael.greaneyed.ac.uk

D. McAusland, S. Seo, D. G. Pintori, J. Finlayson, M. F. Greaney, Org. Lett., 2011, 13, 3667-3669.

DOI: 10.1021/ol201413r (free Supporting Information)



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Abstract

The addition of N-tosyl hydrazones to arynes, generated through fluoride activation of 2-(trimethylsilyl)phenyl triflate precursors, leads to efficient N-arylation. Addition of a Lewis acid to the same reaction pot then affords N-tosylindole products via Fischer cyclization.

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Key Words

Fischer Indole Synthesis, Indoles


ID: J54-Y2011-2020