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Synthesis of 2-Vinylic Indoles and Derivatives via a Pd-Catalyzed Tandem Coupling Reaction

Aude Fayol, Yuan-Qing Fang and Mark Lautens*

*Davenport Research Laboratories, Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, Ontario M5S 3H6, Canada, Email: mlautenschem.utoronto.ca

A. Fayol, Y.-Q. Fang, M. Lautens, Org. Lett., 2006, 8, 4203-4206.

DOI: 10.1021/ol061374l (free Supporting Information)



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Abstract

A novel one-step synthesis of valuable 2-vinylic indoles and their tricycle derivatives occurs via an efficient Pd-catalyzed tandem Buchwald-Hartwig/Heck reaction using a gem-dibromovinyl unit as a readily available starting material.


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Pd-Catalyzed Tandem C-N/C-C Coupling of gem-Dihalovinyl Systems: A Modular Synthesis of 2-Substituted Indoles

Y.-Q. Fang, M. Lautens, Org. Lett., 2005, 7, 3549-3552.


Key Words

Buchwald-Hartwig Coupling, Heck Reaction, Indoles


ID: J54-Y2006-2760