Beilstein J. Org. Chem.2021,17, 83–88, doi:10.3762/bjoc.17.8
directly from readily available alcohols.
Keywords: alcohols; benzothiazolium salts; deoxygenative reactions; fluorine; perfluoroalkylthiolation; thioethers; Introduction
The incorporation of fluorine-containing groups into organic molecules to modulate their biological or physical properties is nowadays
the vast majority of cases, the SRF group is not installed as an intact functional group but rather indirectly through perfluoroalkylation of a thiol or sulfide moiety already present on the substrate (Scheme 1a) [15][20][21][22][23][24][25][26]. By contrast, direct perfluoroalkylthiolation, which
avoids pre-functionalization of the substrate, has been hindered by the lack of suitable reagents. In recent years, however, a selection of mostly electrophilic and radical sources has been introduced [27]. Nucleophilic perfluoroalkylthiolation is especially challenging due to the low nucleophilicity of
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Graphical Abstract
Scheme 1:
Synthetic routes towards perfluoroalkyl thioethers.
Beilstein J. Org. Chem.2010,6, 880–921, doi:10.3762/bjoc.6.88
groups. The reactions are more problematic however, for electron deficient substrates where competing halogenation, reduction and isomerization products often result from perfluoroalkylthiolation reactions.
3.2. Nucleophilic introduction of SRF groups
Anionic salts of type RFS− M+ and their heavy metal
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Graphical Abstract
Figure 1:
Examples of industrial fluorine-containing bio-active molecules.