School of Pharmacy &, Collaborative Innovation Center for Respiratory Disease Diagnosis and Treatment &, Chinese Medicine Development of Henan Province, Henan University of Chinese Medicine, Zhengzhou, 450046, P. R. China.
College of Chemistry and Chemical Engineering, Xinyang Normal University, Xinyang, 464000, P. R. China.
ChemSusChem. 2019 Sep 6;12(17):3960-3966. doi: 10.1002/cssc.201901856. Epub 2019 Aug 13.
By employing tert-butyl nitrite as both nitrogen source and oxidant, the trifluoromethyloximation of alkenes proceeds smoothly in a free-radical process. The developed difunctionalization reaction enables practical and efficient synthesis of a wide range of α-CF ketoximes in moderate yields with excellent regioselectivity. This method features the use of readily available and stable alkenes as substrates and inexpensive CF SO Na as a CF reagent, no involvement of transition metals or external oxidant, and room-temperature conditions. Moreover, a scale-up of the reaction, further transformation of the products into various valuable CF -containing compounds, and removal of the trifluoromethyl group are readily achieved.
采用叔丁基亚硝酸作为氮源和氧化剂，通过自由基过程，烯烃的三氟甲氧基化反应能够顺利进行。所开发的双官能团化反应以中等收率、极好的区域选择性实现了广泛的 α-CF 酮肟的实用且高效合成。该方法的特点是使用易得且稳定的烯烃作为底物，以及廉价的 CF SO Na 作为 CF 试剂，不涉及过渡金属或外加氧化剂，并且在室温条件下进行。此外，该反应能够进行放大，产物能够进一步转化为各种有价值的含 CF 化合物，并且易于脱除三氟甲基。
