Asymmetric Hydrovinylation of 1,3-Dienes

Ohio State University, The, Columbus OH

Investigators

Abstract

In this project supported by the Chemical Catalysis program of the Chemistry Division, Professor RajanBabu aims to develop efficient and selective new reactions of readily available starting materials such as ethylene and simple 1,3-dienes for the production of valuable chemical intermediates. These intermediates could be used for the synthesis of pharmaceutical, agricultural and polymer products. Through an approach that relies on the preparation of new catalysts, and detailed study of reactions, the PI's group addresses two significant challenges: activation of stable molecules to enhance their reactivity and high selectivity in their reactions. Search for solutions to such challenging problems can provide opportunities to make fundamental discoveries having an impact in the field of catalysis. The interdisciplinary nature of this research, which covers the areas of organic, inorganic and organometallic chemistry, and employs the techniques from analytical, physical organic and computational chemistry, provides a valuable platform for training students at every level. 1,3-Dienes such as butadiene and isoprene are readily accessible starting materials that have been used only rarely for the synthesis of fine chemicals. Low reactivity of simple alkyl or aryl substituted dienes and their conformational mobility are largely responsible for this dearth of activity in this area. The PI's group recently developed the first examples of highly enantioselective cobalt-catalyzed additions of ethylene to a wide variety of 1,3-dienes. Extensions of these innovative methods provide highly reactive new intermediates that are useful for elaboration into medicinally relevant compounds. Proposed research to expand the scope of starting materials further enhances the power of this method in organic synthesis by decreasing the synthetic steps required to prepare complex molecules. Since ethylene can be derived from bio-ethanol, these methods add to the repertoire of sustainable processes. The PI is involved in the introduction of a research module to a sophomore laboratory. The experiments in this module are carefully chosen to familiarize a large class with some modern aspects of organic chemistry that relate to selectivity and sustainability.