Design, synthesis, and applications of a uniquely multi-functionalized small organoboron molecule for organic synthesis

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In this project funded by the Chemical Synthesis Program of the Chemistry Division, Professor Takashi Tomioka of the Department of Chemistry at University of Mississippi will explore the synthetic applications of a unique, multi-functionalized small organoboron molecule, diaminoboryl acetonitrile. Despite its structural simplicity as well as potential importance, no study for its use in organic synthesis has been developed. The deprotonation of the acidic hydrogen on the methylene carbon of diaminoboryl acetonitrile with an appropriate base should generate a novel, nucleophilic alpha-diaminoboryl carbanion species that could be utilized for a variety of practical applications in chemical synthesis. Installing and transforming functionalities on organic molecules are the most fundamental and crucial technologies in chemical synthesis, which is needed to address the ever-increasing demand on complex organic molecules. This project intends to develop new and efficient synthetic methodology based on the unique chemistry of diaminoboryl acetonitrile. If successful, it will positively impact any area of activities where the synthesis of organic molecules is needed. These areas of activities include the pharmaceutical, agrochemical, and specialty chemical industries. The project will also provide excellent trainings to the graduate students and undergraduate students involved, including those currently underrepresented in Chemistry.