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
Org. Lett., 2005, 7 (16), pp 3549–3552
DOI: 10.1021/ol051286l
Publication Date (Web): July 9, 2005
Copyright © 2005 American Chemical Society
*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, mlautens@chem.utoronto.ca

Abstract

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2-Substituted indoles were synthesized via a Pd-catalyzed tandem C−N/Suzuki−Miyaura coupling from readily prepared ortho-gem-dihalovinylanilines. Optimal conditions used a Pd(OAc)2/S-Phos catalyst in the presence of K3PO4·H2O and an organoboron reagent, which included boronic acids, esters, alkyl 9-BBN derivatives, and trialkylboranes. Yields of the desired indoles were good to excellent using low catalyst loadings (typically 1 mol %).

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History

  • Published In Issue August 04, 2005
  • Received June 1, 2005

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