Fluorination

Living Edition
| Editors: Jinbo Hu, Teruo Umemoto

N-Haloimide/HF Dethiofluorination

  • Manabu Kuroboshi
  • Tamejiro Hiyama
Living reference work entry
DOI: https://doi.org/10.1007/978-981-10-1855-8_3-1

Introduction

Synthetic methods for organofluorine compounds[1] are categorized roughly into two types [2]: (1) fluorination and (2) use of fluorinated building blocks. Fluorination is further classified into three classes depending on the nature of fluorinating species: (1) electrophilic fluorination (from C-H to C-F using F2 or electrophilic agents), (2) nucleophilic fluorination (from C-Lv (Lv: leaving group) to C-F using fluoride reagents), and (3) deoxofluorination (replacement of hydroxyl or carbonyl groups with one or two fluorides, respectively).

Nucleophilic fluorination is the most accessible reaction, since fluoride ion reagents are stable and easy to handle. However, a fluoride ion is a hard base and poor nucleophile, although bifluoride F - (HF) and dihydrogen trifluoride F - (HF) 2are deemed better nucleophiles. Accordingly, a reactive enough leaving group is essential for successful nucleophilic fluorination. Halogens (Cl, Br, and I), tosylates, and/or triflates are often...
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Copyright information

© Springer Nature Singapore Pte Ltd. 2018

Authors and Affiliations

  1. 1.Department of Applied Chemistry, Faculty of EngineeringOkayama UniversityOkayamaJapan
  2. 2.Research and Development InitiativeChuo UniversityBunkyo-kuJapan