Novel types of stable carbenes and their applications

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With the support of the Chemical Synthesis Program of the Chemistry Division, Professor Guy Bertrand of the Chemistry Department at the University of California - Riverside, will prepare several novel classes of carbenes, the isolation of which have been impeded by the belief that they are inherently unstable, or have eluded the synthetic skills of investigators. These species have not only been chosen because they represent exciting synthetic challenges but more importantly because they should feature interesting electronic and steric properties, which can lead to important applications. These carbenes will be used for the activation of small molecules and enthalpically strong bonds, tasks previously exclusive to transition metal complexes. They will also be utilized for the stabilization of radicals and triplet diradicals based on main group elements, especially phosphorus and boron. Imines derived from these carbenes will allow for the preparation of very strong neutral bases and hydride donors, compounds that are of great interest for organic synthesis. These carbenes are original ligands for transition metal catalysts, and over the years the success of homogeneous catalysis can be attributed largely to the development of a diverse range of ligand frameworks that have been used to tune the behavior of the various systems. It is of paramount importance for the future to find catalysts able to transform abundant and cheap molecules into useful compounds ranging from bulk chemicals to therapeutics. The activation of small molecules without transition metal centers offers an alternative paradigm in the continuing search for efficient catalytic systems, and should allow for considerably reducing the cost of important chemical processes. Additionally, this project is at the interface between physical, organic and organometallic chemistry and is therefore well suited to the education of scientists at all levels. The University of California- Riverside, classified as a minority serving institution, is well positioned to provide the highest quality educational experience for students underrepresented in science. Because of this fact, a diverse group of students will be involved in the project. This research will also promote collaborative research and the exchange of undergraduates, and graduates students between UC Riverside and several French universities.