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

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概要

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• 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 treatment of 1 with KI in the presence of a catalytic amount of CuI gave (Z)-2-fluoro-1-iodo-1-alkenes (3). Pd-catalyzed cross-coupling reactions of 3 gave better results than that of 1, and a variety of (Z)-2-fluoro-1-alkene derivatives were synthesized in good yields.

• Elsevier Ltdの論文
• 2006-09-04

著者

• Hara Shoji

  Div. Of Chemical Process Engineering Graduate School Of Engineering Hokkaido Univ. 8 Kita 13-jo Nish

• Yoshida Masanori

  Div. Of Chemical Process Engineering Graduate School Of Engineering Hokkaido Univ. 8 Kita 13-jo Nish

関連論文

• Stereoselective synthesis of fluoroalkenes via (Z)-2-fluoroalkenyliodonium salts
• Stereoselective synthesis of (Z)-β-fluoro-α,β-unsaturated esters from (Z)-2-fluoro-1-alkenyliodonium salts
• Fluorination of Ketones Using Iodotoluene Difluoride
• α-Fluorination of β-dicarbonyl compounds using p-iodotoluene difluoride under neutral conditions

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