One-Pot Synthesis and Asymmetric Oxidation of 2-Nitro-4-(Trifluoromethyl)Benzene Containing Sulfides

Abstract

An efficient one-pot method for the preparation of 2-nitro-4-(trifluoromethyl)benzene containing sulfides from 1,1′-disulfanediylbis[2-nitro-4-(trifluoromethyl)benzene] is proposed. The corresponding enantiomerically enriched sulfoxides with up to 78% enantiomeric excess are prepared by the asymmetric oxidation of sulfides using a modified Sharpless method. The yield of sulfoxides is shown to decrease with an increase in the bulk of the aliphatic group and with a decrease of the inductive effect of the hydrocarbonic moiety on the sulfur atom.

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GRAPHICAL ABSTRACT

Keywords:

• Fluorinated sulfides
• fluorinated sulfoxides
• asymmetric sulfoxidation
• Sharpless method

Acknowledgements

This work was supported by the RFBR (the project 10-03-00969) and programs of basic researches BGTC-01 (the project 09-Т-3-1015). The authors wish to thank V. Polukeev (CJSC «Vekton») for the generous loan of the corresponding disulfide.