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Catalyst- and Additive-Free Trifluoromethylselenolation with [Me4N][SeCF3]
ACS Sustainable Chemistry & Engineering ( IF 8.4 ) Pub Date : 2017-11-21 00:00:00 , DOI: 10.1021/acssuschemeng.7b03673
Tao Dong 1 , Jian He 2 , Zhi-Han Li 1 , Cheng-Pan Zhang 1, 2
Affiliation  

Environment-benign trifluoromethylselenolation of alkyl halides, electron-deficient aryl halides, diaryliodonium triflates, aryldiazonium tetrafluoroborates, and α-diazo carbonyls with the readily accessible [Me4N][SeCF3] salt is described. A large number of structurally diversified substrates, previously trifluoromethylselenolated by metal-SeCF3 complex or under metal-mediated catalysis at elevated temperatures, were smoothly converted in this reaction at room temperature or −40 °C to room temperature without using any catalyst or additive. Yields of the reactions were comparative to or even higher than those of the early reports employing transition metal catalysts. Compared to the known means, advantages of this method include simplicity, sustainability, high speed, low reaction temperatures, mild reaction conditions, a wide range of substrates, and good functional group tolerance. This catalyst- and additive-free protocol allows a mild and straightforward synthesis of various trifluoromethyl selenoethers and demonstrates the possibility of trifluoromethylselenolation with [Me4N][SeCF3] under greener conditions.

中文翻译:

[Me 4 N] [SeCF 3 ]的无催化剂和无添加剂的三氟甲基硒化

描述了烷基卤,缺电子的芳基卤,二芳基碘鎓三氟甲磺酸盐,芳基重氮四氟硼酸盐和α-重氮羰基与易获得的[Me 4 N] [SeCF 3 ]盐的环境友好的三氟甲基硒化。大量结构多样的底物,先前被金属-SeCF 3进行了三氟甲基硒化在室温下或−40°C到室温下,该络合物或在高温下在金属介导的催化作用下均能平稳转化,而无需使用任何催化剂或添加剂。该反应的产率与使用过渡金属催化剂的早期报道相当或什至更高。与已知方法相比,该方法的优点包括简单,可持续性,高速,低反应温度,温和的反应条件,广泛的底物和良好的官能团耐受性。这种无催化剂和无添加剂的方案允许温和而直接地合成各种三氟甲基硒醚,并证明了在绿色条件下用[Me 4 N] [SeCF 3 ]进行三氟甲基硒化的可能性。
更新日期:2017-11-21
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