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Activation of Alkyl Halides via a Silver-Catalyzed Carbene Insertion Process

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journal contribution
posted on 15.07.2003, 00:00 by H. V. Rasika Dias, R. Greg Browning, Sharon A. Polach, Himashinie V. K. Diyabalanage, Carl J. Lovely
The silver complex [HB(3,5-(CF3)2Pz)3]Ag(THF) featuring a highly fluorinated tris(pyrazolyl)borate ligand catalyzes the formation of aliphatic carbon−halogen bond activation products under remarkably mild conditions. For example, the reaction between CHCl3 and ethyl diazoacetate (EDA) at room temperature in the presence of the silver catalyst afforded HClC(CO2Et)CCl2H in 60% yield. The presence of β-hydrogens on the alkyl halide leads to net hydrogen halide addition to the carbene and an alkene.