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Aliphatic [18F]Fluorination Chemistry for Positron Emission Tomography Read chapter Read first chapter

2020 | OriginalPaper | Chapter

BF3 Fluorination for Preparing Alkyl Fluorides

Authors : Chang-Hua Ding, Xue-Long Hou

Published in: Fluorination

Publisher: Springer Singapore

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Excerpt

Monofluorination is an important access to introduce fluorine atom into organic molecules, which is realized by the strategies employing diethylaminosulfur trifluoride (DAST), tris(diethylamino)sulfonium difluorotrimethylsilicate (TAS-F), hydrogen fluoride, etc. as reagents as shown in other entries of the book. BF3.OEt2 as an ubiquitous reagent is usually used as a Lewis acid in synthetic organic transformations. However, BF3·OEt2 may also serve as an effective nucleophilic fluoride source in the fluorination reaction owing to the property of boron to form ate complex with some Lewis bases and anions. The mechanism of BF3 for fluoride transfer possibly involves a migration of the fluoride via an ate complex readily generated, trifluoroborate with the form of BF3X− (X = Lewis base). Because of its high fluoride content and easy handling in the reaction, the use of BF3·OEt2 as a fluorine source has attracted great attention of synthetic chemists. A comprehensive review has appeared regarding the application of boron trifluoride in the monofluorination reaction [1]. This entry will focus on some synthetically useful applications of BF3 in the synthesis of alkyl fluorides, and some recent examples are included. …

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previous chapter Balz-Schiemann Reaction
next chapter Chemistry of BrF3 Constructing the CF2, CF3 and CF2H Groups
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Metadata
Title
BF3 Fluorination for Preparing Alkyl Fluorides
Authors
Chang-Hua Ding
Xue-Long Hou
Copyright Year
2020
Publisher
Springer Singapore
Book
Fluorination

Print ISBN: 978-981-10-3895-2

Electronic ISBN: 978-981-10-3896-9

Copyright Year: 2020

DOI
https://doi.org/10.1007/978-981-10-3896-9_43

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