Synthesis of 4-Trifluoromethylated 1,3-Butadienes via Palladium Catalyzed Heck Reaction,Chinese Journal of Chemistry

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Synthesis of 4-Trifluoromethylated 1,3-Butadienes via Palladium Catalyzed Heck Reaction
Chinese Journal of Chemistry ( IF 5.5 ) Pub Date : 2021-07-05 , DOI: 10.1002/cjoc.202100313
Yang Li ₁ , Meng Hao ₁ , Yu‐Chen Chang ₁ , Yuan Liu ₁ , Wen‐Fei Wang ₁ , Ning Sun ₁ , Wen‐Qing Zhu ₁ , Ziwei Gao _{2,

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Affiliation

1,3-Butadiene plays a key role in modern synthetic chemistry and biochemistry because it is a key intermediate in the synthesis of many drugs. A new and effective method for the synthesis of 4-trifluoromethylated 1,3-butadiene through the fluorinated Heck reaction catalyzed by Pd(0) is described. Without additives, 1-chloro-3,3,3-trifluoropropene (an inexpensive CF₃ structural unit that is harmless to ozone) reacts with enamide to synthesize 4-trifluoromethylated 1,3-butadienes with good yield, high regioselectivity and chemical selectivity, and strong tolerance of substrate functional groups such as alkynes, aldehyde, and ester groups.

中文翻译：

钯催化 Heck 反应合成 4-三氟甲基化 1,3-丁二烯

1,3-丁二烯在现代合成化学和生物化学中起着关键作用，因为它是许多药物合成的关键中间体。描述了一种通过 Pd(0) 催化的氟化 Heck 反应合成 4-三氟甲基化 1,3-丁二烯的新方法。在没有添加剂的情况下，1-氯-3,3,3-三氟丙烯（一种对臭氧无害的廉价CF ₃结构单元）与烯酰胺反应合成4-三氟甲基化1,3-丁二烯，具有良好的收率、高区域选择性和化学选择性，对炔、醛、酯基等底物官能团的耐受性强。

更新日期：2021-07-05

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