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Updated: Jun 30, 2026

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
Published on: January 19, 2016
Nucleophilic fluorination of triflates by tetrabutylammonium bifluoride
Kyu-Young Kim1, Bong Chan Kim, Hee Bong Lee
1Chemical Development Division, LG Life Sciences, Ltd., R&D Park, 104-1 Moonji-dong, Yusung-gu, Daejeon 305-380, Korea.
Abstract:
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.
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