Designing Ligand Platforms of Titanium Imido Catalysts and Statistically Screening Alkyne Substrates for [2+2+1] Regioselective Pyrrole Synthesis

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Project Summary/Abstract Substituted pyrroles are pivotal organic building blocks in pharmaceuticals, materials, and natural products, however, these scaffolds are often difficult targets. Recently, a titanium imido complex was found to be effective in catalyzing [2+2+1] synthesis of pyrroles using simple alkyne and diazene starting materials. This three-component oxidative coupling offers a new methodology for catalytic pyrrole synthesis and has the potential to be a valuable synthetic tool for organic synthesis of pharmaceuticals and natural products containing a pyrrole core. This research proposal seeks to expand this work by improving regioselective synthesis of pyrroles via catalyst control and to improve rates of reaction by tuning electronic properties of ancillary ligands by modulating arylchalcogenides. In addition, dinitrogen will also be utilized as a new nitrogen source for pyrrole synthesis.