Palladium-Catalyzed Transient Directing Group-Enabled Functionalization of Aliphatic Amines and Aldehydes

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The Chemical Synthesis Program of the Chemistry Division supports the project by Professor Haibo Ge of the Department of Chemistry and Chemical Biology at Indiana University-Purdue University. Amines are organic compounds derived from ammonia by replacement of one or more hydrogen atoms by organic groups. Amines are very common in biology such as in amino acids and neurotransmitters including epinephrine, norepinephrine, dopamine, serotonin, and histamine. The goal of this research is to convert simple amines into other, more valuable or useful amines. To solve this challenge, Professor Ge and his students are using "directing groups" that attach reversibly to the amine group and force the reaction to occur on a specific (desired) site. The summer undergraduate research program attracts college students, especially women and underrepresented minorities, to the STEM areas, training potential future leaders in scientific research. The engagement of high school teachers provides an active learning environment and enables them to deliver in-depth knowledge of key scientific ideas and practices to their classes. This educational effort, in turn, triggers high school students' curiosity, inspires their interest in chemistry, and attracts more high school students into the STEM areas.The Chemical Synthesis Program of the Chemistry Division supports the project by Professor Haibo Ge of the Department of Chemistry and Chemical Biology at Indiana University-Purdue University Indianapolis (IUPUI). Professor Ge is developing new methods to construct carbon-carbon and carbon-heteroatom bonds. This reaction chemistry allows for various common organic compounds to be readily accessed in an efficient manner via a C-H bond functionalization process. It also enables rapid late-stage functionalization (LSF) of complex organic molecules. When compared to conventional cross-coupling reactions, the C-H functionalization process does not require pre-functionalized starting materials and can avoid the use of stoichiometric organometallic reagents, making it more environmentally and economically beneficial. The new type of C-H functionalization reactions allows for the use of readily-available organic molecules as starting materials, and thus improves the potential applications of the process. The principal goal of the project is to develop novel transition metal-catalyzed C-H functionalization reactions in order to provide powerful, valuable, and straightforward synthetic approaches to access common organic frameworks. A variety of medically important (hetero)cyclic skeletons are expected to be efficiently accessed from readily-available aliphatic amines and aldehydes via this strategy. The asymmetric functionalization of these strong sp3 C-H bonds is also designed with the use of chiral catalysts. The project focuses primarily on synthetic organic and organometallic chemistry with potential integration of computational and medicinal chemistry. Thus, the project is well-positioned for the education and training of all levels of scientists. Additionally, an outreach program with high school teachers is designed to enable them to deliver in-depth knowledge of key scientific ideas and practices to their classes.This award reflects NSF's statutory mission and has been deemed worthy of support through evaluation using the Foundation's intellectual merit and broader impacts review criteria.