Fluorination

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| Editors: Jinbo Hu, Teruo Umemoto

α,α-Difluorobenzylamines Deoxofluorination

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DOI: https://doi.org/10.1007/978-981-10-1855-8_49-1
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Introduction

α,α-Difluorobenzylamines are an important class of “N-CF2R” type deoxofluorination reagents. Among various α,α-difluorobenzylamines with different substitution groups, α,α-difluorobenzyl(dimethyl)amine (DBDA) was first used for the deoxofluorination of simple alcohols and carboxylic acids [1]. However, the deoxofluorination property of DBDA has not been systematically studied, and the thermal stability of DBDA was also not shown. In 2004, N,N-Diethyl-α,α-difluoro(meta-methylbenzyl)amine (DFMBA) was first reported as a deoxofluorination reagent by Hara and coworkers [2]. In the next few years, the deoxofluorination property of DFMBA was well studied. DFMBA is a commercially available colorless liquid with boiling point of 81–83 °C/4 mmHg. Accelerating rate calorimetry analysis (ARC) showed that it is stable at temperatures up to 180 °C and decomposes gradually at 210 °C [3]. However, DFMBA can be destroyed gradually by moisture in air; thus, it must be stored in the...

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Authors and Affiliations

  1. 1.Key Laboratory of Organofluorine Chemistry, Center for Excellence in Molecular SynthesisShanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of SciencesShanghaiChina