[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; Gunda I Georg

doi:10.1021/jo035658k

[Bis(2-methoxyethyl)amino]sulfur trifluoride, the Deoxo-Fluor reagent: application toward one-flask transformations of carboxylic acids to amides

J Org Chem. 2004 Apr 2;69(7):2573-6. doi: 10.1021/jo035658k.

Authors

Jonathan M White¹, Ashok Rao Tunoori, Brandon J Turunen, Gunda I Georg

Affiliation

¹ Department of Medicinal Chemistry, University of Kansas, 1251 Wescoe Hall Drive, Lawrence, Kansas 60045-7582, USA.

PMID: 15049661
DOI: 10.1021/jo035658k

Abstract

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.

Publication types

Research Support, U.S. Gov't, Non-P.H.S.
Research Support, U.S. Gov't, P.H.S.

MeSH terms

Amides / chemistry*
Carboxylic Acids / chemistry*
Combinatorial Chemistry Techniques*
Fluorides / chemistry*
Hydrocarbons, Fluorinated
Molecular Structure
Peptides / chemistry
Sulfur Compounds / chemistry*

Substances

(bis(2-methoxyethyl)amino)sulfur trifluoride
Amides
Carboxylic Acids
Hydrocarbons, Fluorinated
Peptides
Sulfur Compounds
Fluorides

Abstract

Publication types

MeSH terms

Substances

Grants and funding