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Synthesis 2002(17): 2561-2578
DOI: 10.1055/s-2002-35626
SPECIALTOPIC
© Georg Thieme Verlag Stuttgart · New York

Recent Advances in Nucleophilic Fluorination Reactions of Organic Compounds­ Using Deoxofluor and DAST

Rajendra P. Singh, Jean’ne M. Shreeve*
Department of Chemistry, University of Idaho, Moscow, ID 83844-2343, USA
Fax: +1(208)8859416; e-Mail: jshreeve@uidaho.edu;
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Publication History

Received 25 September 2002
Publication Date:
20 November 2002 (online)

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Abstract

Selective fluorination of organic compounds continues to be a stimulating and exciting area of research. While a variety of fluorinating reagents and methodologies have been developed to fulfill the increasing demand for site selective fluorination of organic compounds, applications of Deoxofluor and DAST continue to be used widely. Our interest in applying synthetic methods for introducing fluorine or a fluorinated group into a large variety of organic compounds encouraged this review which highlights recent progress in fluorination reactions using Deoxofluor [bis(2-methoxyethyl)aminosulfur trifluoride] and DAST (diethylaminosulfur trifluoride) as key nucleophilic fluorinating reagents. This review covers the literature for fluorination reactions of organic compounds using Deoxofluor and DAST from January 1999 through July 2002.

  • 1 Introduction

  • 2 Synthesis of Deoxofluor [Bis(2-methoxyethyl)aminosulfur Trifluoride] and DAST (Diethylaminosulfur Trifluoride)

  • 3 Fluorination Reactions with Deoxofluor and DAST

  • 3.1 Alcohols, Amino Alcohols, and Diols

  • 3.2 Carbohydrates

  • 3.3 Aldehydes and Ketones

  • 3.4 Dicarbonyls

  • 3.5 Sulfides, Sulfoxides, Thioesters and Thiocarbonyls

  • 3.6 Carboxylic Acids and Acid Chlorides

  • 3.7 Glyoxal Hydrates and Anhydrous Glyoxals

  • 3.8 Epoxides (Oxiranes)

  • 3.9 Peptides

  • 3.10 Ketoximes

  • 4 Miscellaneous Reactions

  • 4.1 Synthesis of Functionalized Oxazolines and Oxazoles

  • 4.2 Synthesis of Amides from Carboxylic Acids

  • 4.3 Synthesis of Cholest-5-ene-3β,4β-diyl Diacetate (Steroid)

  • 4.4 Cycloetherization

  • 5 Reaction Mechanisms Using Deoxofluor and DAST

  • 5.1 Alcohols

  • 5.2 Aldehydes and Ketones

  • 5.3 Carboxylic Acids

  • 5.4 Sulfoxides

  • 5.5 Glyoxal Hydrates

  • 5.6 Ketoximes

  • 6 Conclusions

Key words

Deoxofluor - DAST - nucleophilic reactions - fluorination - halogenation