Nucleophilic fluorination of triflates by tetrabutylammonium bifluoride.
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.
Kim
Kyu-Young
KY
Chemical Development Division, LG Life Sciences, Ltd., R&D Park, 104-1 Moonji-dong, Yusung-gu, Daejeon 305-380, Korea.
Kim
Bong Chan
BC
Lee
Hee Bong
HB
Shin
Hyunik
H
D002625:Chemistry, Organic / Q000379:methods; D005461:Fluorine / Q000737:chemistry; D054879:Halogenation; D000644:Quaternary Ammonium Compounds / Q000737:chemistry*
D000644:Quaternary Ammonium Compounds; D005461:Fluorine; C009405:tetrabutylammonium