Value Added Products from Feedstock Chemicals: Cobalt Catalyzed Asymmetric Hydroboration of 2-Alkyl-1,3-Dienes

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2018-03

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Research Projects

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Abstract

Olefins, one of the most abundantly obtained class of feedstocks from the petroleum refining industry, are starting carbon units for many of the processes used to produce value-added chemicals in the pharmaceutical, agrochemical and polymer industry. However, many of these processes are often limited with harsh reaction conditions, poor yields and low selectivities. Organic chemists have long been trying to address the unmet challenges in this field; to simultaneously activate and functionalize olefins under mild reaction conditions, with the desired level of precision and selectivity, in order to access high value-added molecules from cheap and abundant lower alkenes. By employing transition metal catalysts as powerful tools, we sought to address olefin functionalization, more specifically carbon-boron bond forming reactions, which could provide a powerful means to access a broad range of advanced, highly functionalized target molecules of interest to medicinal chemistry and related areas. We sought to develop a highly efficient catalytic protocol using the earth abundant metal, cobalt, linked to suitable ligands, to achieve the hydroboration of unactivated olefins to obtain organo-borane products with desired level of yield and selectivity. The operationally simple, yet unprecedented reactions we discovered expand the realm of hydrofunctionalizations to provide direct access to a number of boranes, of interest in organic synthesis.

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Poster Division: Engineering, Math, and Physical Sciences: 3rd Place (The Ohio State University Edward F. Hayes Graduate Research Forum)

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Transition Metal Catalysis Methodology Development

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