A high hydroarylation activity of K₂PtCl₄/AgOTf catalyst in the reaction of propiolic acid with unactivated and activated arenes

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• 作者：Juzo Oyamada ; Takuya Hashimoto ; Tsugio Kitamura
• 关键词：Platinum catalyst ; Hydroarylation ; Alkyne ; cis-Cinnamic acid ; Propiolic acid
• 刊名：Journal of Organometallic Chemistry
• 出版年：2009
• 出版时间：15 October 2009
• 年：2009
• 卷：694
• 期：22
• 页码：3626-3632
• 全文大小：258 K

文摘

A mixed catalyst K₂PtCl₄/AgOTf showed the highest activity for hydroarylation of propiolic acid, among palladium and platinum catalysts. This catalyst was effective for hydroarylation with less reactive benzene to give cis-cinnamic acid in good yield. The hydroarylation with toluene gave a higher yield of hydroarylation products than that with benzene and resulted in ortho/para orientation with an almost statistical ratio, suggesting that the result is very close to that of the Friedel-Crafts alkylation with methyl bromide or p-nitrobenzyl chloride. Hydroarylation of propiolic acid with other electron-rich arenes proceeded efficiently in the presence of the K₂PtCl₄/AgOTf catalyst in trifluoroacetic acid forming cis-cinnamic acids in good to high yields. This method was also applied to hydroarylation of ethyl propiolate.