AsianScientist (Jan. 4, 2018) – A research group at the Institute of Basic Science (IBS) in South Korea have devised a method to selectively introduce aryl groups into carbon-hydrogen (C-H) bonds at room temperature. They published their work in the journal Nature Chemistry,
Carbon-carbon (C-C) bonds make up the skeleton of all organic molecules. However, creating such ubiquitous C-C bonds artificially is still a complicated task. In particular, since several molecules used in medicine, pharmacology and material chemistry contain aryl groups, devising a way to efficiently and selectively introduce this chemical group is a major goal for organic chemists. Currently, most arylation reactions require harsh reaction conditions, including high temperatures and excess additives.
In this study, researchers at the Center for Catalytic Hydrocarbon Functionalization at IBS managed to introduce aryl groups at specific locations within organic compounds at room temperature. Their method consisted of three main steps.
Firstly, an iridium catalyst was used to activate a substrate that contains C-H bonds. Secondly, the activated substrate attacks the iridium, creating an intermediate molecule with iridium at its center. The third step involved oxidizing the iridium center of the intermediate, which the researchers showed was essential to achieving arylation at room temperature. The proposed reaction mechanism was verified with electroparamagnetic resonance, cyclic voltametry and computer simulations.
“Developing a more efficient and environmentally benign oxidation system is our next goal,” said Dr. Shin Kwangmin of IBS, who is first author of the study.
The article can be found at: Shin et al. (2017) Iridium-catalysed Arylation of C–H Bonds Enabled by Oxidatively Induced Reductive Elimination.
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Source: Institute for Basic Science; Photo: Shutterstock.
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