Acceptor-Acceptor Carbenoids in Selective Insertions and Cyclizations

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With this award, the Chemical Synthesis Program is supporting Professor Jon Rainier at the University of Utah to study the conversion of vinyl diazophosphonates and diazo vinylphosphonates into acceptor-acceptor Rh carbenes and use the carbenes in insertion reactions with alcohols, amines, and thiols. Included in this work will be the examination of novel substrates and reactions having unique properties. The inspiration for many of these substances and reactions came from both naturally and non-naturally occurring small molecules that have been shown to be biologically active. As a consequence, these studies will generate new materials of potentially high impact in the chemical and pharmaceutical industry. Professor Rainier will integrate the research and educational components of this project into the teaching curriculum at the University of Utah as well as into his work with the American Chemical Society Student Affiliates. By bringing research projects into the undergraduate curriculum, Professor Rainier hopes to inspire the next generation of scientists to careers in chemistry. Through his involvement with the Student Affiliates, Professor Rainier has reached out to many elementary and middle school students through hands on experiments, workshops and demonstrations in an attempt to promote curiosity and STEM education. In this research, new methods involving acceptor-acceptor vinyl carbenes will be developed for the synthesis of phosphonate containing materials and small molecules. The work that will be carried out in pursuit of these goals is unique in that it will both provide a better fundamental understanding of the properties of phosphonate containing carbenes and in that it will have practical value. Professor Rainier and his group will explore the effect of electronic and steric perturbations on metal carbenes and substrates on the insertion chemistry of vinyl diazophosphonates. Over the course of this work, a range of phosphonate-containing small molecules will be generated. Preliminary evidence suggests that these products may have potential as bioactive small molecules and as ligands for functionalized iron nanoparticles, themselves with possible application in the delivery of small molecules and genes in biological systems.