Trifluoromethylation of Electron-Rich Alkenyl Iodides with Fluoroform-Derived "Ligandless" CuCF3

Trifluoromethylation of Electron-Rich Alkenyl Iodides with Fluoroform-Derived "Ligandless" CuCF3

J. Mestre, A. Lishchynsky, S. Castillón, O. Boutureira
J. Org. Chem. 2018, 83, 8150-8160.

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.

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