Palladium-Catalyzed, Modular Synthesis of Highly Functionalized Indoles and Tryptophans by Direct Annulation of Substituted o-Haloanilines and Aldehydes

Yanxing Jia and Jieping Zhu*
Institut de Chimie des Substances Naturelles, CNRS, 91198 Gif-sur-Yvette Cedex, France
J. Org. Chem., 2006, 71 (20), pp 7826–7834
DOI: 10.1021/jo061471s
Publication Date (Web): September 6, 2006
Copyright © 2006 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.

, zhu@icsn.cnrs-gif.fr

Abstract

Abstract Image

One-pot synthesis of indoles by a palladium-catalyzed annulation of ortho-haloanilines and aldehydes has been developed. Coupling of ortho-iodoaniline with aldehyde is realized under mild ligandless conditions [Pd(OAc)2, DABCO, DMF, 85 °C], whereas X-Phos is found to be the ligand of choice for coupling reactions involving ortho-chloroanilines/ortho-bromoanilines and aldehydes. A variety of ortho-haloanilines with different electronic properties are suitable substrates, and aldehydes including chiral ones participated in this reaction without racemization. Coupling of (S)-2-N,N-di-tert-butoxycarbonyl-5-oxopentanoate, derived from l-glutamic acid, with ortho-haloanilines provides a rapid access to the ring-A-substituted tryptophans in good to excellent yields.

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History

  • Published In Issue September 29, 2006
  • Received July 15, 2006

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