Organic synthesis and materials chemistry via catalytic organoborane chemistry

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The ability to prepare complex organic molecules efficiently has been critical in the development of the pharmaceutical industry. Recently, similar abilities have become important in areas such as liquid crystals and organic electronics. In this case, the molecules employed must be free of isomers and other contaminants that may impact performance. Thus, state-of-the-art synthetic techniques to prepare molecules for materials applications is critical. In the case of pharmaceutical applications of organic molecules, the most urgent need is for new structures that have not been made previously and may have unique physiological activities. For these reasons, we propose to examine the synthesis of two novel classes of molecules with applications in the pharmaceutical and materials areas. Chiral 1,1-diaryl alkanes are molecules that are exceedingly difficult to make by existing routes, yet these provide novel chiral scaffolds that are of interest to the pharmaceutical industry and materials chemistry. Likewise, the chiral 1,1,1-triarylmethanes and alkanes are virtually unknown in their enantiomerically pure state. We have proposed routes to prepare these important classes of compounds based on recent chemistry from our lab. The routes provide compounds of >95% optical and isomeric purity. In our second area of research, we propose to employ frustrated Lewis pair (FLP) chemistry for the activation of alkane C-H bonds. When an acidic and a basic molecule are present in solution but are inhibited (usually by sterics) from reacting with each other they are said to be a Frustrated Lewis Pair. In this case, the molecules can cooperate to split relatively unreactive bonds such as H-H, H-Si and H-B. We plan to employ this method for the activation of C-H bonds, which is a critical goal in terms of synthesis and energy since effective C-H activation strategies could better utilize petroleum feedstocks. Initially we will use organic structures that are biased towards the desired reaction in order to demonstrate feasibility, but we plan to move toward organic molecules with less and less functionality. HQP involved in this chemistry will gain a wide range of expertise in the area of organic synthesis, catalysis, air sensitive techniques and materials chemistry.