Abstract
A mixed catalyst K 2PtCl 4/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 K 2PtCl 4/AgOTf catalyst in trifluoroacetic acid forming cis-cinnamic acids in good to high yields. This method was also applied to hydroarylation of ethyl propiolate.
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