Nucleophilic fluorination of triflates by tetrabutylammonium bifluoride

KY Kim, BC Kim, HB Lee, H Shin

Index: Kim, Kyu-Young; Bong, Chan Kim; Hee, Bong Lee; Shin, Hyunik Journal of Organic Chemistry, 2008 , vol. 73, # 20 p. 8106 - 8108

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Citation Number: 35

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 ...