An Efficient Synthesis of Achiral and Chiral 1,2,4-Triazolium Salts:  Bench Stable Precursors for N-Heterocyclic Carbenes

Mark S. Kerr, Javier Read de Alaniz, and Tomislav Rovis*
Department of Chemistry, Colorado State University, Fort Collins, Colorado 80523 rovis@lamar.colostate.edu
J. Org. Chem., 2005, 70 (14), pp 5725–5728
DOI: 10.1021/jo050645n
Publication Date (Web): June 14, 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.

Abstract

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The promising utility of triazolyl N-heterocyclic carbene catalysts in umpolung aldehyde chemistry requires a straightforward reliable synthesis from readily available materials. Herein, we describe the synthesis of a variety of triazolyl N-heterocyclic carbene precursors. The reactions commence from commercially available amino acids and proceed in 44−68% overall yields. The N-heterocyclic salts are air-stable crystalline solids that can be stored with no special precaution and can generate the active catalyst when treated with an appropriate base.

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History

  • Published In Issue July 08, 2005
  • Received April 1, 2005

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