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Deoxytrifluoromethylthiolation and Selenylation of Alcohols by Using Benzothiazolium Reagents
Author(s) -
Dix Stefan,
Jakob Michael,
Hopkinson Matthew N.
Publication year - 2019
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201901607
Subject(s) - reagent , chemistry , fluorine , organic chemistry , combinatorial chemistry
Abstract Aliphatic compounds substituted with medicinally important trifluoromethylthio (SCF 3 ) and trifluoromethylselenyl (SeCF 3 ) groups were synthesized directly from alcohols by using the new benzothiazolium salts BT‐SCF 3 and BT‐SeCF 3 . 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‐SCF 3 proceeds under mild conditions and the similarly efficient trifluoromethylselenylation reactions using BT‐SeCF 3 are, to the best of our knowledge, the first reported examples of this transformation.