CAREER: SusChEM: New Methods for Cu-Catalyzed Cross-Coupling Reactions

Indiana University, Bloomington IN

Investigators

Abstract

In this (CAREER) project funded by the Chemical Catalysis Program of the Chemistry Division, Professor Michael K. Brown of the Department of Chemistry at Indiana University is introducing new methods for the catalytic construction of carbon-carbon bonds, which is an important objective in modern organic chemistry. The overarching goal of this research is to utilize inexpensive copper (Cu)-catalysts to assist in the synthesis of useful molecules such as new pharmaceutical agents. This new catalytic method promotes sustainability by using first row (non-precious metal) copper catalysts. Such catalyst are more abundant, less toxic and less environmentally harmful than precious metal catalysts. The educational goal is accomplished by developing engaging chemistry-themed classroom activities and by evaluating, improving and replicating a permanent chemistry-themed exhibit at a children's museum recently developed by the Brown Lab. These activities introduce and connect a known concept, smell, to something unknown, chemical structure. Professor Brown's efforts meet two needs in science education: development of chemistry-themed exhibits at science museums, and introduction of chemistry to children at a young age. Professor Brown is developing two general classes of Cu-catalyzed methods for carbon-carbon bond formation: 1) Suzuki-Miyaura-type cross-coupling reactions, and 2) Suzuki-Miyaura-type cross-coupling reactions that are interrupted by an alkene. Implementation of these methods enables chemists in academia and industry to access complex molecular scaffolds that were previously difficult to prepare. The impacts and intellectual merit of these studies are expected to be the following: 1) introduction of inexpensive, sustainable Cu-catalysts for Suzuki-Miyaura-type cross-couplings, 2) discovery of new methods for the functionalization of readily available unactivated alkenes, and 3) uncovering new modes of reactivity with Cu-catalysts. This research promotes sustainable chemistry by using first row (non-precious metal) copper catalysts. The educational goal is accomplished by developing fun and engaging organic chemistry-themed classroom activities and by evaluating, improving and replicating a permanent organic chemistry themed exhibit at a children's museum recently developed by the Brown Lab. These activities introduce and connect a known concept, smell, to something unknown, chemical structure. As the educational component of his project, Professor Brown is developing materials that educate children in grades K-6 about very basic concepts related to molecular structure and organic chemistry.