Tetrahedron

Stereoselective synthesis of fluoroalkenes via (Z)-2-fluoroalkenyliodonium salts

M Yoshida, A Komata, S Hara

Index: Yoshida, Masanori; Komata, Ayumu; Hara, Shoji Tetrahedron, 2006 , vol. 62, # 36 p. 8636 - 8645

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Citation Number: 30

Abstract

Stereoselective synthesis of fluoroalkenes is described.(Z)-2-Fluoro-1-alkenyl (phenyl) iodonium tetrafluoroborates (1) were synthesized stereoselectively in good yields by Michael-type addition of HF to 1-alkynyl (phenyl) iodonium tetrafluoroborates (2) with a commercially available HF reagent, hydrofluoric acid or Et3N–3HF. Pd-catalyzed cross- coupling reactions using 1 gave (Z)-2-fluoro-1-alkene derivatives in moderate yields. The ...