The hydrofunctionalization of olefins is a long-standing goal for transition metal catalysis. We have discovered catalysts for the first additions of N-H and O-H bonds to unactivated alkenes and have discovered catalysts for the addition of amines and alcohols to vinylarenes and dienes. Most recently, we have disclosed systems for the addition of boranes to internal alkenes enantioselectively and systems for the first anti-Markovnikov hydroarylations of unactivated alkenes with high regioselectivity. The products of the asymmetric hydroborations lead to enantioenriched amines, alcohols and alkylarenes.
This work on alkene hydrofunctionalization rests upon two discoveries of new elementary reactions for organometallic complexes. We reported the oxidative addition of ammonia to form monomeric products with late transition-metal complexes and the insertions of ethylene and alpha-olefins into transition-metal amido and transition-metal alkoxo bonds.