Intramolecular construction of trifluoromethyl group by the palladium-catalyzed reaction of 2, 3, 3-trifluoroallylic carbonates with O-nucleophiles. Issue 13 (29th March 2018)

• Record Type: Journal Article
• Authors: Hoshino, Yuji; Isa, Kazuki; Hanakawa, Taisyun; Tsuji, Hiroaki; Kawatsura, Motoi
• Is Part Of: Tetrahedron. Volume 74:Issue 13(2018)
• Page Start: 1555
• Page End: 1564
• Publication Date: 2018-03-29
• Subjects: Palladium -- Fluorine -- Trifluoromethyl group -- C-F bond activation -- Enol ether; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2018.02.022
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: The synthesis of the trifluoromethyl group containing enol ethers by the palladium-catalyzed intermolecular reaction of 2, 3, 3-trifluoroallylic carbonates with oxygen nucleophiles was accomplished. The reaction proceeds through the intermolecular attack of oxygen nucleophiles on the C-2 carbon atom of the allylic unit, and the intramolecular fluorine atom shift from the C-2 position to the C-3 position. The reactions with several types of alcohols and phenols proceeded smoothly, and afforded the corresponding trifluoromethyl group containing enol ethers in good to high yields. Graphical abstract: