Rhodium-catalyzed hydroaroylation of ¦Á,¦Â-unsaturated esters using aroyl chlorides and Et₂MeSiH

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• 作者：Takako Muraoka ; Eiji Hiraiwa ; Minami Abe ; Keiji Ueno
• 关键词：Rh-catalyzed ; Three-component coupling ; Aroyl chloride ; Hydrosilane
• 刊名：Tetrahedron Letters
• 出版年：2013
• 出版时间：7 August, 2013
• 年：2013
• 卷：54
• 期：32
• 页码：4309-4312
• 全文大小：596 K

文摘

Hydroaroylation of methyl acrylate 2a to give the ¦Á-aroyl esters 4 took place in the three-component reaction of 2a, aroyl chlorides 1, and Et₂MeSiH in the presence of 1 mol  % of [Rh(cod)(PR₃)₂]OTf (cod = 1,5-cyclooctadiene, OTf = OSO₂CF₃, R = Ph (3a), OPh (3b)) in CH₂Cl₂. GC and ¹H NMR investigation revealed that the rhodium-catalyzed hydroaroylation proceeds via two successive transformations, that is, hydrosilylation of 2a to afford silyl enol ether 5a followed by C-C bond formation between 5a and 1a.