Stereospecific Synthesis of Trifluoromethylated Vinyl Sulfides

Abstract

The synthetic utility of fluorinated vinylstannanes has been explored. This methodology provides a convenient and simple synthesis of trifluoromethylated vinyl sulfides in 60-97% yields with the formation of the E-isomer exclusively. The reaction is stereospecific and of wide scope including various types of thiols (aryl, benzyl, alkyl thiols, and thiols with an ethoxycarbonyl moiety) used as substrates. A possible mechanism is proposed.

Key words

fluorine - thiols - stereoselective synthesis - sulfur - tin

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