Tetrahedron letters

An intriguing effect of Yb (OTf) 3–TMSCl in the halogenation of 1, 1-disubstituted alkenes by NXS: selective synthesis of allyl halides

M Yamanaka, M Arisawa, A Nishida, M Nakagawa

文献索引：Yamanaka, Masamichi; Arisawa, Mitsuhiro; Nishida, Atsushi; Nakagawa, Masako Tetrahedron Letters, 2002 , vol. 43, # 13 p. 2403 - 2406

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被引用次数: 31

摘要

A novel protocol to effect the efficient selective halogenation of 1, 1-disubstituted alkenes with NXS catalyzed by Yb (OTf) 3–TMSCl, which affords the corresponding allyl halides in high yield, including allyl bromide, chloride, iodide and fluoride, is described. A remarkable feature of Yb (OTf) 3–TMSCl-catalyzed halogenation is that, unlike conventional radical halogenation with N-halosuccinimides, the reaction discriminates between the allylic and ...