α-Trifluoromethyl Carbanion-catalyzed Intermolecular Stetter Reaction of Aromatic Aldehydes with 2-Bromo-3,3,3-trifluoropropene: Synthesis of β-Alkoxyl-β-trifluoromethylated Ketones,Organic Letters

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α-Trifluoromethyl Carbanion-catalyzed Intermolecular Stetter Reaction of Aromatic Aldehydes with 2-Bromo-3,3,3-trifluoropropene: Synthesis of β-Alkoxyl-β-trifluoromethylated Ketones
Organic Letters ( IF 4.9 ) Pub Date : 2021-12-17 , DOI: 10.1021/acs.orglett.1c03553
Yingying Cai ₁ , Huanfeng Jiang ₁ , Chuanle Zhu ₁

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The intermolecular Stetter reaction of aromatic aldehydes with 2-bromo-3,3,3-trifluoropropene is achieved by the in situ generated α-trifluoromethyl carbanion catalyst. It not only represents the first example for α-trifluoromethyl carbanion-catalyzed umpolung reaction but also reveals a new protocol for the umpolung of aldehydes. Various useful β-alkoxyl-β-trifluoromethylated ketones were obtained in high yields, which could further convert to attractive bioactive compounds. Mechanism studies indicated an intramolecular 1,4-shift of the hydrogen atom was involved in this reaction.

中文翻译：

α-三氟甲基碳负离子催化芳香醛与 2-Bromo-3,3,3-三氟丙烯的分子间取代反应：β-烷氧基-β-三氟甲基化酮的合成

芳香醛与2-溴-3,3,3-三氟丙烯的分子间Stetter反应是通过原位生成的α-三氟甲基碳负离子催化剂实现的。它不仅代表了 α-三氟甲基碳负离子催化的 umpolung 反应的第一个例子，而且还揭示了醛的 umpolung 的新方案。以高产率获得了各种有用的β-烷氧基-β-三氟甲基化酮，可进一步转化为有吸引力的生物活性化合物。机理研究表明，该反应涉及氢原子的分子内 1,4 位移。

更新日期：2022-01-14

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