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


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Please use this identifier to cite or link to this item:http://hdl.handle.net/2115/14704

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

OAI-PMH ( junii2 , jpcoar_1.0 )

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