[Bis(2-methoxyethyl)amino]sulfur Trifluoride, the Deoxo-Fluor Reagent:  Application toward One-Flask Transformations of Carboxylic Acids to Amides

Jonathan M. White, Ashok Rao Tunoori, Brandon J. Turunen, and Gunda I. Georg*
Department of Medicinal Chemistry, University of Kansas, 1251 Wescoe Hall Drive, Lawrence, Kansas 60045-7582 %georg@ku.edu
J. Org. Chem., 2004, 69 (7), pp 2573–2576
DOI: 10.1021/jo035658k
Publication Date (Web): March 4, 2004
Copyright © 2004 American Chemical Society
*

 Corresponding author.

Abstract

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The use of the Deoxo-Fluor reagent is a versatile method for acyl fluoride generation and subsequent one-flask amide coupling. It provides mild conditions and facile purification of the desired products in good to excellent yields. We have explored the utility of this reagent for the one-flask conversion of acids to amides and Weinreb amides and as a peptide-coupling reagent.

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History

  • Published In Issue April 02, 2004
  • Received November 10, 2003

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