Nucleophilic Fluorination of Triflates by Tetrabutylammonium Bifluoride
Kyu-Young Kim, Bong Chan Kim, Hee Bong Lee* and Hyunik Shin*
*Chemical Development Division, LG Life Sciences, Ltd., R&D
Park, 104-1 Moonji-dong, Yusung-gu, Daejeon 305-380, Korea, Email: hbonglee
lgls.com,
hisinlgls.com
K.-Y. Kim, B. C. Kim, H. B. Lee, H. Shin, J. Org. Chem., 2008, 73, 8106-8108.
DOI: 10.1021/jo8015659
Abstract
A nucleophilic fluorination of triflates by weakly basic tetrabutylammonium bifluoride provides excellent yields with minimal formation of elimination-derived side products. Most primary and secondary hydroxyl groups are excellent substrates, but benzylic and aldol-type secondary hydroxyl groups give poor yields as a result of the instability of their triflates.
see article for more examples
Key Words
Fluoroalkanes, Benzyl Fluorides
ID: J42-Y2008-3100
