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Copper-Catalyzed Difluoromethylation of Aryl Iodides with (Difluoromethyl)zinc Reagent

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journal contribution
posted on 21.07.2016, 14:38 by Hiroki Serizawa, Koki Ishii, Kohsuke Aikawa, Koichi Mikami
The combination of difluoroiodomethane and zinc dust or diethylzinc can readily lead to (difluoromethyl)zinc reagents. Therefore, the first copper-catalyzed difluoromethylation of aryl iodides with the zinc reagents is accomplished to afford the difluoromethylated arenes. The reaction proceeds efficiently through the ligand/activator-free operation without addition of ligands for copper catalyst (e.g., phen and bpy) and activators for zinc reagent (e.g., KF, CsF, and NaO-t-Bu). Moreover, transmetalation of the CF2H group from zinc reagent to copper catalyst proceeds even at room temperature to form the cuprate [Cu­(CF2H)2].