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3.20.1.1 Stereoselective Electrophilic Fluorination

DOI: 10.1055/sos-SD-203-00543

Gouverneur, V.; Lozano, O.Science of Synthesis: Stereoselective Synthesis, (20113852.

For the stereoselective synthesis of monofluorinated compounds, electrophilic fluorination processes outnumber methods that use nucleophilic fluorinating reagents. Common reagents for electrophilic fluorination are the user-friendly N-fluoro reagents, such as 1-(chloromethyl)-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate) (1, Selectfluor), N-fluorobenzenesulfonimide [2, NFSI, N-fluorobis(phenylsulfonyl)amine], N-fluorobenzene-1,2-disulfonimide (3, NFOBS, 2-fluoro-1,3,2-benzodithiazole 1,1,3,3-teroxide),[‌9‌] and N-fluoropyridinium salts (e.g., 4)[‌10‌] (Scheme 1). The preparation of N-fluorobenzene-1,2-disulfonimide (3) is outlined in Scheme 2.

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