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Hydroxylation of Aliphatic and Aromatic C-H Bonds Catalyzed by Biomimetic Transition-metal Complexes

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SOC SYNTHETIC ORGANIC CHEM JPN
DOI: 10.5059/yukigoseikyokaishi.80.506

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transition-metal complex; reactive oxidant; hydrogen peroxide; peracid; aliphatic C-H activation; aromatic hydroxylation

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This article discusses the applications of hydroxylation reactions in both chemical and biological fields. By studying metalloenzymes in living organisms, we can understand how these enzymes achieve selective oxidation reactions of hydrocarbons. The article summarizes the achievements of our laboratory in designing highly selective and efficient oxidation reactions.
Hydroxylation of hydrocarbons is a simple chemical transformation reaction. However, this is not an easier task than it looks in the chemical equations. The reactions generally require harsh (high temperature, high pressure, strongly acidic, or basic) conditions, which induce over oxidation giving a complicated mixture of products. In contrast, living organisms perform such difficult tasks like selective oxidation of methane to methanol and benzene to phenol by employing appropriate oxidizing species generated using earth abundant transition metals (Fe and Cu) in the well-organized reaction centers of metallo-monooxygenases. We have been trying to understand the essence of the chemical functions of such metalloenzymes to construct selective and efficient oxidation reactions of inert aliphatic and aromatic compounds. In this article, our recent accomplishments in this endeavor are summarized together with the backgrounds of the related chemistry.

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