Highly Chemoselective Hydrogenolysis of Iodoarenes

Abstract

The catalytic hydrodehalogenation reaction using molecular hydrogen and Pd/C has been revisited. It is shown that the speed of removal of halogen increases with increasing electronegativity I < Br < Cl. Nevertheless, selective dehydrohalogenation in compounds containing other reducible functions can be achieved only with iodine and not with bromine or chlorine. Selective deiodination of iodobenzophenone could be accomplished without reducing the carbonyl group. Hydrogenolysis of azidoiodoaromatic compounds to the corresponding azido compounds is high yielding. This selectivity was exploited for the labeling of benzophenone- and azido-containing compounds by deuterium and tritium.