Trifluoromethylation of Electron-Rich Alkenyl Iodides with Fluoroform-Derived ligandless CuCF3

Identifier:  imarina:6040630

Handle: https://hdl.handle.net/20.500.11797/imarina6040630

Authors:  Mestre, Jordi; Lishchynskyi, Anton; Castillon, Sergio; Boutureira, Omar

Abstract:
© 2018 American Chemical Society. We herein present a flexible approach for the incorporation of CF3 units into a predefined site of electron-rich alkenes that exploits the regiocontrolled introduction of an iodine handle and subsequent trifluoromethylation of the C(sp2)-I bond using fluoroform-derived ligandless CuCF3. 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 CF3-scaffolds, such as sugars, nucleosides (antivirals), and heterocycles (indoles and chromones), with potential for academic and industrial applications.