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Deoxytrifluoromethylthiolation and Selenylation of Alcohols by Using Benzothiazolium Reagents
Stefan Dix1, Michael Jakob1, Matthew N Hopkinson1
1Institute of Chemistry and Biochemistry, Freie Universität Berlin, Takustrasse 3, 14195, Berlin, Germany.
Abstract:
Aliphatic compounds substituted with medicinally important trifluoromethylthio (SCF3 ) and trifluoromethylselenyl (SeCF3 ) groups were synthesized directly from alcohols by using the new benzothiazolium salts BT-SCF3 and BT-SeCF3 . These bench-stable fluorine-containing reagents are facile to use and can be prepared in two steps from non-fluorinated heteroaromatic starting materials. The metal-free deoxytrifluoromethylthiolation process using BT-SCF3 proceeds under mild conditions and the similarly efficient trifluoromethylselenylation reactions using BT-SeCF3 are, to the best of our knowledge, the first reported examples of this transformation.
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