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;
Further Information

Publication History

Publication Date:
08 September 2006 (online)

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

    References

  • For general overviews of fluorine chemistry, see:
  • 1a Shimizu M. Hiyama T. Angew. Chem. Int. Ed.  2005,  44:  214 
  • 1b Kirsch P. Modern Fluoroorganic Chemistry   Wiley-VCH; Weinheim: 2004. 
  • 1c Special Issue on ‘Fluorine in the Life Sciences’; ChemBio Chem   2004.  5:  p.557 
  • 2a Singh RP. Shreeve JM. Synthesis  2002,  2561 
  • 2b Singh RP. Meshria DT. Shreeve JM. In Advances in Organic Synthesis, Atta-ur-Rahman   Bentham Science Publishers; 2006.  2:  p.291 
  • 3a Lal GS. Pez GP. Pesaresi RJ. Prozonic FM. Chem. Commun.  1999,  215 
  • 3b Lal GS. Pez GP. Pesaresi RJ. Prozonic FM. Cheng H. J. Org. Chem.  1999,  64:  7048 
  • 4 Singh RP. Shreeve JM. J. Fluorine Chem.  2002,  116:  23 
  • 5 Krow GR. Lin G. Moore KP. Thomas AM. DeBrosse C. Ross CWIII. Ramjit HG. Org. Lett.  2004,  6:  1669 
  • 6 Mase T. Houpis IN. Akao A. Dorziotis I. Emerson K. Hoang T. Iida T. Itoh T. Kamei K. Kato S. Kato Y. Kawasaki M. Lang F. Lee J. Lynch J. Maligres P. Molina A. Nemoto T. Okada S. Reamer R. Song JZ. Tschaen D. Wada T. Zewge D. Volante RP. Reider PJ. Tomimoto K. J. Org. Chem.  2001,  66:  6775 
  • 7 Lal GS. Lobach E. Evans A. J. Org. Chem.  2000,  65:  4830 
  • 8a Singh RP. Twamley B. Shreeve JM. J. Org. Chem.  2002,  67:  1918 
  • 9 Tunoori AR. White JM. Georg GI. Org. Lett.  2000,  2:  4091 
  • 10a Phillips AJ. Uto Y. Wipf P. Reno MJ. Williams DR. Org. Lett.  2000,  2:  1165 
  • 10b Mahler SG. Serra GL. Antonowb D. Mantaa E. Tetrahedron Lett.  2001,  42:  8143