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Synlett 2006(15): 2515-2516  
DOI: 10.1055/s-2006-950419
SPOTLIGHT
© Georg Thieme Verlag Stuttgart · New York

Deoxo-Fluor [Bis(2-methoxyethyl)aminosulfur Trifluoride]: An Advanced Nucleophilic Fluorinating Reagent in Organic Synthesis

Xihe Bi*
Department of Chemistry, Northeast Normal University, Changchun 130024, P. R. of China
e-Mail: drxhbi@gmail.com;
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Publication History

Publication Date:
08 September 2006 (online)

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Introduction

Organofluorine compounds have had a marked impact on medical and organochemical fields and the number of ­applications continues to grow. [1] These significant contributions arise from the unique changes that occur in the physical and chemical properties of ordinary organic compounds due to the presence of a fluorine-containing group. The use of Deoxo-FluorTM [N(MeOCH2CH2)2SF3] as a nucleophilic fluorinating reagent is gaining popu­larity. [2] Compared with DAST (Et2NSF3), the traditional deoxofluorinating agent, Deoxo-FluorTM is thermally less instable and thus more amenable to large-scale use. So far, it has been predominantly applied to convert alcohols, [3-5] ­aldehydes, ketones, [3a,6] glyoxalates [8] and carboxylic acids [9] into the ­corresponding monofluoromethyl and difluoro­methylene derivatives. Also, conversion of thiocarbonyl derivatives to fluorinated products has been achieved. [7] In addition to its role as fluorinating reagent, Deoxo-FluorTM played an important role in inducing cyclizations of β-hydroxy amides (thioamides) to corresponding oxazolines (thi­azolines). [10]

Deoxo-FluorTM can be obtained by reacting the N-trimethylsilyl derivative of bis(2-methoxyethyl)amine with SF4 in Et2O at -30 °C (Scheme 1). [3]

Scheme 1 Preparation of Deoxo-FluorTM