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Beilstein J. Org. Chem. 2022, 18, 872–880, doi:10.3762/bjoc.18.88
Graphical Abstract
Scheme 1: Electrochemical gem-difluorination of sulfides bearing α-electron-withdrawing groups.
Scheme 2: Electrochemical gem-difluorodesulfurization of dithioacetals.
Scheme 3: Electrochemical gem-difluorodesulfurization of dithiocarbonate.
Scheme 4: Cathodic reduction of 1.
Figure 1: Cyclic voltammograms of (a) PhSCF2Br (1, 8 mM) in 0.1 M n-Bu4NClO4/MeCN; (b) o-phthalonitrile (4 mM...
Scheme 5: Indirect cathodic reduction of 1 using o-phthalonitrile as mediator.
Scheme 6: Mechanism for the formation of product 3.
Scheme 7: Reaction of compound 1 with PhS anions.
Scheme 8: Cathodic reduction of compound 1 in the presence of α-methylstyrene at a high current density.
Scheme 9: Indirect cathodic reduction of compound 1 in CD3CN.
Scheme 10: Indirect cathodic reduction of compound 1 in the presence of 1,1-diphenylethylene.
Scheme 11: Reaction mechanism.
Beilstein J. Org. Chem. 2018, 14, 389–396, doi:10.3762/bjoc.14.27
Figure 1: Cyclic voltammograms of 0.1 M Bu4NBF4/MeCN with a Pt disk working electrode in the absence (brown l...
Figure 2: Calculated HOMO diagram of 1a.
Figure 3: Calculated HOMO diagrams of 1h, 1i and 1j.
Scheme 1: Plausible reaction paths of the anodic oxidation of 1i in Et4NF·4HF/CH2Cl2.
Scheme 2: Anodic fluorination of 1k.
Scheme 3: Anodic fluorination of cyclic derivative 1l.
Scheme 4: Anodic oxidation of 1m and 1n in Et4NF·4HF/CH2Cl2.
Scheme 5: General reaction mechanism for the anodic fluorination of 1.
Scheme 6: Reaction mechanism for the anodic oxidation of carboxylic acids 1m and 1n in the presence of a fluo...
Beilstein J. Org. Chem. 2015, 11, 85–91, doi:10.3762/bjoc.11.12
Scheme 1: Anodic fluorination of sulfides having an electron-withdrawing group.
Scheme 2: Anodic fluorination of dithioacetals.
Figure 1: Dependency of fluorinated product selectivity on a series of fluoride salts (a) Et3N·nHF (n = 3–5) ...
Scheme 3: Plausible reaction mechanism for anodic fluorination of 1b, 1d, and 1f.
Scheme 4: Mechanism for suppression of the elimination of HF (deprotonation) and preferable desulfurization o...