Mestre Jordi, Lishchynskyi Anton, Castillón Sergio, Boutureira Omar
Departament de Química Analítica i Química Orgànica , Universitat Rovira i Virgili , C/Marcel·lí Domingo 1 , 43007 Tarragona , Spain.
Institute of Chemical Research of Catalonia (ICIQ) , The Barcelona Institute of Science and Technology (BIST) , Av. Països Catalans 16 , 43007 Tarragona , Spain.
J Org Chem. 2018 Aug 3;83(15):8150-8160. doi: 10.1021/acs.joc.8b00927. Epub 2018 Jul 2.
We herein present a flexible approach for the incorporation of CF units into a predefined site of electron-rich alkenes that exploits the regiocontrolled introduction of an iodine handle and subsequent trifluoromethylation of the C(sp)-I bond using fluoroform-derived "ligandless" CuCF. The broad substrate scope and functional group tolerance together with the scalability and purity of the resulting products enabled the controlled, late-stage synthesis of single regioisomers of complex CF-scaffolds, such as sugars, nucleosides (antivirals), and heterocycles (indoles and chromones), with potential for academic and industrial applications.
我们在此展示了一种灵活的方法，可将CF单元引入富电子烯烃的预定义位点，该方法利用碘处理基团的区域控制引入以及随后使用源自氟仿的“无配体”CuCF对C(sp)-I键进行三氟甲基化。广泛的底物范围和官能团耐受性，以及所得产物的可扩展性和纯度，使得能够可控地、后期合成复杂CF支架的单一区域异构体，如糖、核苷（抗病毒药物）和杂环化合物（吲哚和色酮），具有学术和工业应用潜力。
