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Synthesis of 3-trifluoromethylated 1,3-butadienes via a Pd(0)-catalyzed fluorinated Heck reaction
Reaction Chemistry & Engineering ( IF 3.9 ) Pub Date : 2020-03-25 , DOI: 10.1039/d0re00093k
Yang Li 1, 2, 3, 4 , Meng Hao 1, 2, 3, 4 , Ming Xia 4, 5, 6, 7 , Ning Sun 1, 2, 3, 4 , Cai-Lin Zhang 1, 2, 3, 4 , Wen-Qing Zhu 1, 2, 3, 4
Affiliation  

1,3-Butadienes play a key role in modern synthetic chemistry and biochemistry because they are well-known precursors for the synthesis of retinoids. A new and efficient synthesis of 3-trifluoromethylated 1,3-butadienes via a Pd(0)-catalyzed fluorinated Heck reaction is described. Without an additive, the reaction of 2-bromo-3,3,3-trifluoropropene, an abundant and ozone friendly CF3 building block, with acrylamides afforded 3-trifluoromethylated 1,3-butadienes in good to excellent yields with high regioselectivity and s-trans/s-cis ratios under mild conditions. Inspired by the concept of space–time yield for continuous reactions, the average space–time yield calculated shows that all the reactions far exceed 1 g gcat−1 h−1, which is high enough for further scale-up, suggesting that small amounts of catalyst and a very small reactor are required.

中文翻译:

通过Pd(0)催化的氟化Heck反应合成3-三氟甲基化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,因为它们是类视黄醇合成的众所周知的前体。描述了通过Pd(0)催化的氟化Heck反应合成3-高效三氟甲基化1,3-丁二烯的新方法。如果没有添加剂,2-溴-3,3,3-三氟丙烯(一种丰富且对臭氧无害的CF 3结构单元)与丙烯酰胺的反应可提供3-三氟甲基化的1,3-丁二烯,产率高至优异,且具有较高的区域选择性和s -在温和条件下反式/顺式-顺式比率。受连续反应的时空产率概念的启发,计算出的平均时空产率表明,所有反应均超过1 g gcat -1h -1足够高以进一步扩大规模,这表明需要少量的催化剂和非常小的反应器。
更新日期:2020-03-25
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