Ligand Free Palladium‐Catalyzed Synthesis of α‐Trifluoromethylacrylic Acids and Related Acrylates by Three‐Component Reaction,Advanced Synthesis & Catalysis

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Ligand Free Palladium‐Catalyzed Synthesis of α‐Trifluoromethylacrylic Acids and Related Acrylates by Three‐Component Reaction
Advanced Synthesis & Catalysis ( IF 4.4 ) Pub Date : 2020-01-07 , DOI: 10.1002/adsc.201901446
Pan Xiao ₁ , Xavier Pannecoucke ₁ , Jean‐Philippe Bouillon ₁ , Samuel Couve‐Bonnaire ₁

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Aryl iodides and 2‐(trifluoromethyl)acrylic acid reacted together in ligand‐free Mizoroki‐Heck reaction furnishing a quick and efficient access to highly valuable α‐trifluoromethylacrylic acids. The useful transformation was independent with regard to the electronic nature of the aryl group substituent. A three‐component one‐pot version was also developed to give diverse substituted acrylates. The versatility of α‐trifluoromethylacrylic acids was demonstrated by quick access to 3‐CF₃‐coumarins as well as fluorinated analogues of therapeutic or cosmetic agents. Finally, we proposed a catalytic cycle based on the silver carboxylate salt, identified as a key intermediate in the reaction.

中文翻译：

三组分反应的无配位钯催化的α-三氟甲基丙烯酸及其相关丙烯酸酯的合成

芳基碘化物和2-（三氟甲基）丙烯酸一起在无配体的Mizoroki-Heck反应中反应，可快速有效地获得高价值的α-三氟甲基丙烯酸。就芳基取代基的电子性质而言，有用的转化是独立的。还开发了三组分一锅法版本，以提供各种取代的丙烯酸酯。快速获得3-CF _3-香豆素以及治疗剂或美容剂的氟化类似物证明了α-三氟甲基丙烯酸的多功能性。最后，我们提出了基于羧酸银盐的催化循环，该羧酸银盐被确定为反应中的关键中间体。

更新日期：2020-01-07

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