Novel Reagents and Catalysts for Organic Synthesis

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The generation of chemical space and its translation into new functions is one of the main goals of synthetic chemistry. The BN/CC isosterism (i.e., replacement of a carbon-carbon bond with a boron-nitrogen bond) has emerged as a viable strategy to increase the chemical space of compounds relevant to biomedical research. This proposal describes a program geared toward developing BN isosteres of arenes as useful building blocks, reagents, and catalysts for synthetic organic chemistry and chemical biology applications. Specifically, we seek to: 1) establish azaborines as four-carbon (4C) + 1 nitrogen (1N) + 1 boron (1B) synthon for synthetic applications that exploit the preinstalled functional density of an azaborine, i.e., a nitrogen atom, a boron atom, and a 1,3-butadiene unit to efficiently produce new aminoborylated compounds for diversity-oriented synthesis. 2) establish azaborines as a new family of ligands that can engage in distinct coordination modes with transition metals to affect new reactivity and selectivity in metal-catalyzed transformations. 3) utilize BN-indole and its corresponding amino acid BN-tryptophan to create novel BN-alloproteins and to develop a novel bioconjugation platform that is rapid, catalyst-free, chemoselective, and orthogonal to existing bioconjugation methods. Completion of the proposed aims will yield new fundamental knowledge related to boron in the context of synthetic organic and biological chemistry. It will generate new synthetic methods and research tools for the investigation of biological processes and inspire the design and development of new boron-containing molecules for biomedical applications.