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by Principal Investigator
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Brenton DeBoef, University of Rhode Island
Using monies from the American Chemical Society Petroleum Research Fund, we have discovered new methods for synthesizing carbon-carbon (C-C) bonds using simple unfunctionalized substrates containing carbon-hydrogen (C-H) bonds. In recent years, much effort has been dedicated to the development of methods for directly forming C-C bonds from simple C-H bonds. The majority of this work focuses on the regioselective functionalization of a single C-H bond within a substrate by reacting it with a pre-functionalized reagent in the presence of a metal catalyst. We have discovered a superior method that synthesizes C-C bonds by directly coupling two C-H bonds. Notably, the terminal oxidant for many of these processes is molecular oxygen. Oxidative couplings of this kind are rare, but have high potential impact for the synthesis of valuable molecules such as arylated indoles and benzofurans—substructures that are commonly found in synthetic drugs. Furthermore, we have recently discovered that the regioselectivity of the oxidative couplings that form arylated indoles can be easily controlled by the choice of oxidant in the reaction. Thus far, the PRF Type-G Grant has funded our research, culminating in the publication of two articles and the disclosure of one US patent. We intend to use the remainder of the grant to explore the mechanism of the novel oxidative couplings that we have discovered and to apply these reactions to the synthesis of complex molecules. With the help of this grant from the PRF, we have begun to explore new chemical territory. The work will surely continue after this grant cycle ends, hopefully with support from funding agencies such as the National Science Foundation and the Environmental Protection Agency.
Using monies from the American Chemical Society Petroleum Research Fund, we have discovered new methods for synthesizing carbon-carbon (C-C) bonds using simple unfunctionalized substrates containing carbon-hydrogen (C-H) bonds. In recent years, much effort has been dedicated to the development of methods for directly forming C-C bonds from simple C-H bonds. The majority of this work focuses on the regioselective functionalization of a single C-H bond within a substrate by reacting it with a pre-functionalized reagent in the presence of a metal catalyst. We have discovered a superior method that synthesizes C-C bonds by directly coupling two C-H bonds. Notably, the terminal oxidant for many of these processes is molecular oxygen.
Oxidative couplings of this kind are rare, but have high potential impact for the synthesis of valuable molecules such as arylated indoles and benzofurans—substructures that are commonly found in synthetic drugs. Furthermore, we have recently discovered that the regioselectivity of the oxidative couplings that form arylated indoles can be easily controlled by the choice of oxidant in the reaction.
Thus far, the PRF Type-G Grant has funded our research, culminating in the publication of two articles and the disclosure of one US patent. We intend to use the remainder of the grant to explore the mechanism of the novel oxidative couplings that we have discovered and to apply these reactions to the synthesis of complex molecules. With the help of this grant from the PRF, we have begun to explore new chemical territory. The work will surely continue after this grant cycle ends, hopefully with support from funding agencies such as the National Science Foundation and the Environmental Protection Agency.
With the help of this grant from the PRF, we have begun to explore new chemical territory. The work will surely continue after this grant cycle ends, hopefully with support from funding agencies such as the National Science Foundation and the Environmental Protection Agency.
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