A Versatile Approach Toward the Assembly of Diazirine Functionality Utilizing Bmida

Our research focuses on a cost-effective approach which minimizes synthetic overhead when assembling compounds with diazirine functionality. The goals are to prevent the surplus use of ammonia in the formation of the diaziridines and use an IKA Electrosyn 2.0 in the oxidation of diaziridine. Success with either specific aim will significantly reduce the synthetic overhead currently observed. Diazirine functionality plays a vital role in a vast number of applications. Two of interest to us include diazirine functionality as a next generation propellant and as a photoaffinity label. With the latter, this strategy plays a vital role in drug discovery and biomedical research as it allows researchers to study, understand, manipulate, and control complex biological systems. Moreover, previous research has shown that diazirine functionality has the potential to be used as propellants, so this project also aims to explore the energetic properties of this functionality and develop a deeper understanding of their physical properties. Preliminary data has shown limitations with scope and low to moderate levels of conversion. Our current approach has as a focus, a cross-coupling reaction where scope is only limited by the pairing of N-methyliminodiacetic acid boronate ester (BMIDA) and substrate.