三氟甲基化
电化学
肉桂酸
化学
脱羧
计算化学
组合化学
有机化学
催化作用
物理化学
三氟甲基
电极
烷基
作者
Yoshihiko Yamamoto,Norihiko Goto,Takeshi Yasui,Hiroshi Uchida
标识
DOI:10.1002/asia.202400967
摘要
β-(Trifluoromethyl)styrenes are potentially useful building blocks for the synthesis of organofluorine compounds because their electron-deficient C=C double bonds can undergo diverse transformations. One of the most practical methods for preparing β-(trifluoromethyl)styrenes is the decarboxylative trifluoromethylation of readily available cinnamic acid derivatives using the Langlois reagent as a less expensive trifluoromethyl source. We revisited the electrochemical decarboxylative trifluoromethylation of cinnamic acid derivatives to identify modified conditions that reduce the loading of the Langlois reagent without additional additives. The reaction mechanism was computationally investigated to gain insight into the dependence of the product yields on the aryl terminal groups. The synthetic utility of the obtained β-(trifluoromethyl)styrenes was demonstrated by their transformation into 4-aryl-3-(trifluoromethyl)pyrrolidines.
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