Expeditious trifluoromethylthiolation and trifluoromethylselenolation of alkynyl(phenyl)iodoniums by [XCF3]− (X = S, Se) anions

Abstract

Trifluoromethylthiolation and trifluoromethylselenolation of alkynyl(phenyl)iodonium tosylates by [XCF₃]⁻ (X = S, Se) ions was accomplished in 5–10 minutes at room temperature under a N₂ atmosphere and provided a variety of alkynyl trifluoromethyl sulfides and selenides in good yields. Compared to the known methods, this approach has several advantages such as short reaction times and metal- and additive-free conditions without needing excess [Me₄N][XCF₃] reagents. Moreover, the less efficient reactions of (phenylethynyl)benziodoxol(on)e with [Me₄N][XCF₃] under the standard conditions demonstrate that acyclic alkynyl(phenyl)iodoniums are more powerful alkynyl sources in the conversion. This protocol allows for a fast and convenient access to numerous alkynyl trifluoromethyl sulfides and selenides.