Transition-metal chloride mediated addition reaction of diorganomagnesium to easily enolizable ketones

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• 作者：Mutsumi Sada^a ; Seijiro Matsubara ; ^a ; ^{matsubar@orgrxn.mbox.media.kyoto-u.ac.jp}
• 关键词：Grignard reagent ; Diorganomagnesium ; Organocerium ; Organoytterbium ; Organoiron
• 刊名：Tetrahedron
• 出版年：2011
• 出版时间：8 April 2011
• 年：2011
• 卷：67
• 期：14
• 页码：2612-2616
• 全文大小：337 K

文摘

An alkylation to an easily enolizable ketone, such as β-tetralone, is difficult to perform with Grignard reagent (RMgX) or with diorganomagnesium (R₂Mg), because a deprotonation to form a magnesium enolate occurs predominantly. To avoid the prior enolization, a complex reagent of a transition-metal salt and R₂Mg was examined: A combination of R₂Mg with iron(II) chloride (FeCl₂) or ytterbium(III) chloride (YbCl₃) gave a complex reagent that can realize a nucleophilic reaction to β-tetralone prior to the enolization. A combination of RMgX with these metal salts is inferior to a combination of R₂Mg with them to obtain the nucleophilic complex reagent.