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

Yoshida, Masanori; Komata, Ayumu; Hara, Shoji

Tetrahedron, 2006, 62(36), 8636-8645

Permalink : https://hdl.handle.net/2115/14704

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アクセス権	open access
URI	https://hdl.handle.net/2115/14704
タイトル	Stereoselective synthesis of fluoroalkenes via (Z)-2-fluoroalkenyliodonium salts
著者	Yoshida, Masanori ; Komata, Ayumu ; Hara, Shoji
e-Rad_Researcher 30322829 著者名 Yoshida, Masanori
著者名 Komata, Ayumu
著者名 Hara, Shoji
言語	英語
キーワード	Fluoroalkene
	Alkenyliodonium salt
	Stereoselective synthesis
	Pd catalyst
	Cross-coupling
発行日	2006-09-04
出版者	Elsevier Ltd
収録物名	Tetrahedron
巻(号)	62(36)
ページ	8636-8645
抄録	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.
資源タイプ	学術雑誌論文
出版タイプ	Accepted Manuscript
PISSN	0040-4020
関連情報	URI http://www.sciencedirect.com/science/journal/00404020
関連情報 (isVersionOf)	出版社版DOI https://doi.org/10.1016/j.tet.2006.05.085