Chemoselective Hydrosilylation of Olefin/Ketone Catalyzed by Iminobipyridine Fe and Co complexes

Abstract

Abstract The chemoselective hydrosilylation of olefins and ketones catalyzed by Fe and Co complexes bearing an iminobipyridine derivative ligand was investigated. The reaction of a 1 : 1 mixture of styrene and acetophenone over the Fe catalyst achieved selective hydrosilylation of acetophenone. In contrast, the corresponding Co complex showed the opposite selectivity‐styrene‐selective hydrosilylation. The reaction of 3‐acetylstyrene with both olefin and ketone moieties in the molecule showed that the Co complex catalyzed olefin‐selective hydrosilylation. In contrast, the addition of pyridine to the Co‐catalyzed system showed the opposite chemoselectivity, affording the ketone hydrosilylated product. The chemoselectivity of olefin/ketone hydrosilylation was switched by replacing the central metal of the complex with the iminobipyridine derivative ligand and by changing the simple reaction conditions (absence or presence of pyridine) using an identical Co complex.