Asymmetric Borenium Cations in Catalysis

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Many key products for the pharmaceutical, commodity chemical and agrochemical sectors are chiral compounds produced by reduction chemistry. The production of such materials can be achieved using conventional stoichiometric reductions of suitable precursors, followed by separation of optical isomers. This is a highly an inefficient approach as it severely limits the yield of the desired optically pure materials and generated significant quantities of waste that must be dealt with. An alternative approach is asymmetric hydrogenation of readily available precursors, however current technologies rely on expensive chiral transition metal catalysts derived from precious metals such as Pd, Rh, or Ir. Moreover, residual metals in the product are significant health and environmental concern and thus must be removed. This results in a further and substantial cost to production. In the present proposal, we will develop a new strategy that uses a "metal-free" catalyst technology based on the innovative concept of Frustrated Lewis Pair chemistry discovered by the PI in 2006. Adaptation of this approach for highly selective asymmetric and catalytic reductions will provide a new highly efficient strategy that will reduce cost of production by eliminating by-product waste, removing the necessity of extensive post-production purification and utilize more cost efficient catalysts. The project will be carried out collaboratively at Queen's University and the University of Toronto and involve an industrial collaborators from Pirmal Corporation in Toronto, an international company with a significant research presence in Canada specializing in custom synthesis. The students involved in this work will be trained in catalysis, organic and inorganic chemistry and also acquire a unique perspective on industrial applications of new chemical technologies.