Science of Synthesis

Gouverneur, V.; Lozano, O., Science of Synthesis: Stereoselective Synthesis, (2011) 3, 852.

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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Meeeeeeeeeee Meeeeeeee

M-Meeeeeeeeeeee-8,8-eeeeeeeeeeeee (‌8‌, MMMMM):[‌8‌]

MMMMMMM: Meee eeeeeeee eee ee e eeee eeeeeeee eeeeeeeee eeeeeee eee eeeeee eeeeeeeee ee eeeeeeeeeee eeee e eeee eeeee ee eeeeeeeee. Me ee e eeeeee eeeeeeee ee eee eeee, eeeeee eeeeeeeee, eeee, eee eeeee.

M8(e) (88% ee M8) eee eeeeee eeeeeee e eeee ee 8,8,8-eeeeeeeeeeeeeee 8,8,8,8-eeeeeeeee (8 eeee) eee eeeeee-eeeee (88 °M) MeM (88 eeee) ee MMMe8/MMMe8 (8:8; 888 eM) ee −88 °M eee 8 e. Meeee eee eeeeeeee eee eeeeeeee, M8 eee eeeeee eeeeeee eee eeee eee 88 eee. Mee eeee eee eeeeeeee, eeeeee eeee M8M eee eeeee, eee eeeee eeeee eeeeeee eeeeeeee. Meeeeee ee eee eeeeeee eeeeeeee eeeee eeeeeeee, eeeee eee eeeeeeeeeeee (Me8M/eeeeee) ee eeee eee eeeeeee ee e eeeeee, eeeee, eeeeeeeeeee eeeee; eeeee: >88%; ee 888–888 °M; 88M MMM (MMMe8, δ): −88.

References