Applications of Cyclopropenylidene Metal Complexes and Thioureas in Catalysis

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Our research program combines organic synthesis, computational, and physical organic chemistry directed at the improvement of catalytic processes and the development of new ones. These activities provide mechanistic insight into chemical reactivity, molecular structure, and bonding. Fueling this interest is the widespread use of catalysis in the production of medicinally important natural and unnatural compounds, bulk materials such as polymers, fine chemicals, and energy from both fossil and renewable fuel sources, while advancing more efficient and green manufacturing processes to preserve diminishing resources and protect the environment. Over the next five years our program will focus on the following: (1)We will develop complexes derived from coinage metals (copper, silver, gold) and apply these to a broad spectrum of useful chemical products. Of specific interest will be the use of these complexes in reactions providing unique arrangements of atoms in small rings, activation of chemical bonds that are very reticent to react, and the synthesis of heterocyclic compounds. We anticipate that these complexes will exhibit a number of interesting chemical properties, which we will investigate through the combination of theoretical and spectroscopic techniques. (2)We will develop thiourea-based hydrogen bond catalyst that will be applied to the synthesis of sugars, including C-glycosides, compounds from nature that serve as key motifs in numerous antitumor, antibiotic, and antidiabetic (type II) agents. The synthesis of C-glycosides, which are sugar analogs differing by the subtle presence of a single atom, is of importance because of their stability to metabolism and specific function in cellular tissues. Because C-glycosides last longer in the blood and tissues of patients, they are useful in the design of new drugs. We project this area of discovery will have far-reaching outcomes directly applicable to catalysis, basic chemical understanding, and drug development. In addition to fundamental insight into reaction mechanisms and chemical bonding, the outcome of the proposed research will advance the fields of organic synthesis, catalysis, and material science. Our advancement of an array of metal complexes and thiourea hydrogen bond catalysts will enable new modes of catalysis allowing for efficient synthetic routes to complex natural products, pharmaceutical targets, and value-added chemicals. This research will also provide excellent training for future chemistry professionals both in the pharmaceutical industry and in academia.