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首页> 外文期刊>Chemistry: A European journal >Copper-Catalyzed Trifluoromethylation of Internal Olefinic C-H Bonds: Efficient Routes to Trifluoromethylated Tetrasubstituted Olefins and N-Heterocycles
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Copper-Catalyzed Trifluoromethylation of Internal Olefinic C-H Bonds: Efficient Routes to Trifluoromethylated Tetrasubstituted Olefins and N-Heterocycles

机译：铜催化的内部烯烃C-H键的三氟甲基化：三氟甲基化的四取代的烯烃和N-杂环的有效途径。

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摘要

The functionalization of internal olefins has been a challenging task in organic synthesis. Efficient Cu~(II)-catalyzed trifluoromethylation of internal olefins, that is, α-oxoketene dithioacetals, has been achieved by using Cu(OH)_2 as a catalyst and TMSCF_3 as a trifluoromethylating reagent. The push–pull effect from the polarized olefin substrates facilitates the internal olefinic C-H trifluoromethylation. Cyclic and acyclic dithioalkyl α-oxoketene acetals were used as the substrates and various substituents were tolerated. The internal olefinic C-H bond cleavage was not involved in the rate-determining step, and a mechanism that involves radicals is proposed based on a TEMPO-quenching experiment of the trifluoromethylation reaction. Further derivatization of the resultant CF_3 olefins led to multifunctionalized tetrasubstituted CF_3 olefins and trifluoromethylated N-heterocycles.
机译：内烯烃的官能化一直是有机合成中的一项艰巨任务。通过使用Cu（OH）_2作为催化剂和TMSCF_3作为三氟甲基化试剂，实现了Cu-（II）催化的内烯烃三氟甲基化反应，即α-氧杂环丁烯二硫缩醛的高效反应。极化烯烃底物的推挽效应有助于内部烯烃C-H三氟甲基化。环状和无环二硫代烷基α-氧杂环丁烯缩醛被用作底物，并且容许各种取代基。速率确定步骤不涉及内部烯烃的C-H键裂解，基于三氟甲基化反应的TEMPO猝灭实验，提出了涉及自由基的机理。所得CF 3烯烃的进一步衍生导致多官能化的四取代的CF 3烯烃和三氟甲基化的N-杂环。

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