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

Yuan-Qing Fang and Mark Lautens*

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

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

DOI: 10.1021/ol051286l

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Abstract

The Pd-catalyzed tandem C-N/Suzuki-Miyaura coupling of readily prepared ortho-gem-dihalovinylanilines with boronic acids, esters, alkyl 9-BBN derivatives, and trialkylboranes gave 2-substituted indoles in good to excellent yields. Optimal conditions used low loadings of a Pd(OAc)₂/S-Phos catalyst in the presence of K₃PO₄·H₂O.

see article for more examples

see article for more reactions

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

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

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Key Words

Suzuki Coupling, Buchwald-Hartwig Amination, Indoles

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ID: J54-Y2005-1050