Abstract
The present review covers new efficient conversions (fluorodehydroxylations) of aliphatic primary or secondary hydroxy groups with nonaflyl fluoride ( N-C 4 F 9 SO 2 F; NfF) and bases such as 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), diethylamine, triethylamine or triethylamine trihydrofluoride into their corresponding (inverted) fluoro compounds. The scope, mechanisms and side reactions of these combinations of NfF with different bases are discussed. 1 Introduction 2 The Combination of NfF with DBU 3 Mechanism, Optimization and Economics of the NfF/DBU Combination 4 Side Reactions 4.1 Formation of σ-Complexes 4.2 Formation of Olefins 4.3 Interference by Neighboring Nucleophilic Groups 5 Combinations of NfF with Other Bases 6 The Different Mechanisms of Fluorodehydroxylations with NfF 6.1 With DBU 6.2 With Diethylamine 6.3 With Triethylamine or Diisopropylethylamine and Their Corresponding Trihydrofluorides 7 Summary
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