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Synthesis and Performance Characterizations of Transition Metal Single Atom Catalyst for Electrochemical CO2 Reduction
Published on: April 10, 2018
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Rhoda-Electrocatalyzed Bimetallic C-H Oxygenation by Weak O-Coordination
Xuefeng Tan1, Leonardo Massignan1, Xiaoyan Hou1
1Institut für Organische und Biomolekulare Chemie, Georg-August-Universität Göttingen, Tammannstraße 2, 37077, Göttingen, Germany.
Angewandte Chemie (International Ed. in English)
|March 2, 2021
Summary
Bimetallic rhodium electrocatalysis enables direct C-H oxygenation of arenes using amides and ketones. This method also achieves selective synthesis of dihydrooxazinones through twofold C-H functionalization.
Area of Science:
- Organic Chemistry
- Electrochemistry
- Catalysis
Background:
- Direct C-H functionalization remains a significant challenge in organic synthesis.
- Electrocatalysis offers a sustainable alternative for driving chemical transformations.
- Rhodium catalysis is known for its efficacy in C-H activation reactions.
Purpose of the Study:
- To develop a novel rhodium-electrocatalyzed method for arene C-H oxygenation.
- To achieve selective synthesis of dihydrooxazinones via twofold C-H functionalization.
- To elucidate the mechanism of the electrooxidation-induced C-H activation.
Main Methods:
- Bimetallic rhodium electrocatalysis.
- Controlled application of electrical current.
- Mechanistic studies employing mass spectroscopy and cyclovoltammetric analysis.
Main Results:
- Successful C-H oxygenation of arenes using weakly O-coordinating amides and ketones.
- Selective synthesis of diverse dihydrooxazinones.
- Demonstration of twofold C-H functionalization enabled by current control.
- Evidence for an unprecedented electrooxidation-induced C-H activation pathway.
Conclusions:
- Bimetallic rhodium electrocatalysis is effective for direct arene C-H oxygenation.
- The developed method provides access to valuable dihydrooxazinone scaffolds.
- The study reveals a novel mechanism involving electrooxidation-induced C-H activation.
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