178552-83-5Relevant academic research and scientific papers
Versatile application of trifluoromethyl triflate
Kolomeitsev, Alexander A.,Vorobyev, Mikhail,Gillandt, Hartmut
, p. 449 - 454 (2008/09/18)
Hydrolytically stable and easy to handle trifluoromethyl triflate was found to be a liquid reservoir of 'masked' difluorophosgene. Anhydrous F- sources cleave the S-O bond in trifluoromethyl triflate yielding quantitatively the trifluoromethanolate salts, being useful trifluoromethoxy group carriers. Reaction of trifluoromethanolates with in situ generated from o-trimethylsilylphenyl triflate benzyne leads to (trifluoromethoxy)benzene and fluorobenzene (ratio 85:15). Whereas an addition of trifluoromethanethiolate anion across a triple bond of benzyne leads to [(trifluoromethyl)sulfanyl]benzene solely.
Nucleophilic fluorination of triflates by tetrabutylammonium bifluoride
Kim, Kyu-Young,Bong, Chan Kim,Hee, Bong Lee,Shin, Hyunik
, p. 8106 - 8108 (2008/12/22)
(Chemical Equation Presented) Careful examination of nucleophilicity, basicity, and leaving group ability led us to discover the nucleophilic fluorination of triflates by weakly basic tetrabutylammonium bifluoride, which provides excellent yields with minimal formation of elimination-derived side products. Primary hydroxyl groups as well as secondary hydroxyl groups in acyclic chains or in five-membered rings are excellent substrates, whereas benzylic and aldol-type secondary hydroxyl groups give poor yields as a result of the instability of their triflates.
