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

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Title: Stereoselective synthesis of fluoroalkenes via (Z)-2-fluoroalkenyliodonium salts
Authors: Yoshida, Masanori Browse this author →KAKEN DB
Komata, Ayumu Browse this author
Hara, Shoji Browse this author
Keywords: Fluoroalkene
Alkenyliodonium salt
Stereoselective synthesis
Pd catalyst
Cross-coupling
Issue Date: 4-Sep-2006
Publisher: Elsevier Ltd
Journal Title: Tetrahedron
Volume: 62
Issue: 36
Start Page: 8636
End Page: 8645
Publisher DOI: 10.1016/j.tet.2006.05.085
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 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.
Relation: http://www.sciencedirect.com/science/journal/00404020
Type: article (author version)
URI: http://hdl.handle.net/2115/14704
Appears in Collections:工学院・工学研究院 (Graduate School of Engineering / Faculty of Engineering) > 雑誌発表論文等 (Peer-reviewed Journal Articles, etc)

Submitter: 吉田 雅紀

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