Palladium-Catalysed Carbon-Fluorine and Carbon-Hydrogen Bond Alumination of Fluoroarenes and Heteroarenes
Created: 2017-06-15 10:23
Last modified: 2017-08-15 10:18
Through serendipitous discovery, a palladium bis(phosphine) complex was identified as a catalyst for the selective transformation of sp2C–F and sp2C–H bonds of fluoroarenes and heteroarenes to sp2C–Al bonds (19 examples, 1 mol% Pd loading). The carbon–fluorine bond functionalization reaction is highly selec-tive for the formation of organoaluminum products in preference to hydrodefluorination products (selectivity = 4.4:1 to 27:1). Evidence is presented for a two step mechanism in which hydrodefluorination is followed by sp2C–H alumination.