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Palladium-Catalyzed Synthesis of 2-Cyanoindoles from 2-gem-Dihalovinylanilines

Nicolas Zeidan, Sabine Bognar, Sophia Lee and Mark Lautens*

*Davenport Research Laboratories, Department of Chemistry, University of Toronto, Toronto, Ontario M5S 3H6, Canada, Email: mlautenschem.utoronto.ca

N. Zeidan, S. Bognar, S. Lee, M. Lautens, Org. Lett., 2017, 19, 5058-5061.

DOI: 10.1021/acs.orglett.7b02244 (free Supporting Information)


Abstract

2-Cyanoindoles are found in many natural products and have high bioactivity. In an efficient Pd(0)-catalyzed synthesis of 2-cyanoindoles from 2-gem-dihalovinylanilines, Zn(TFA)2 is used to prolong the catalytic activity. Additionally, the amount of cyanide in the reaction phase is minimized due to the better solubility of Zn(CN)2 in a two-solvent mixture.


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proposed mechanism



Key Words

indoles


ID: J54-Y2017