Concise Report
Electrochemically Enabled Intramolecular Aminooxygenation of Alkynes via Amidyl Radical Cyclization
Zhong-Wei Hou,
Hai-Chao Xu,
Zhong-Wei Hou
State Key Laboratory of Physical Chemistry of Solid Surfaces, iChEM, Key Laboratory of Chemical Biology of Fujian Province, and College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, Fujian, 361005 China
Search for more papers by this authorCorresponding Author
Hai-Chao Xu
State Key Laboratory of Physical Chemistry of Solid Surfaces, iChEM, Key Laboratory of Chemical Biology of Fujian Province, and College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, Fujian, 361005 China
E-mail: [email protected]Search for more papers by this authorZhong-Wei Hou,
Hai-Chao Xu,
Zhong-Wei Hou
State Key Laboratory of Physical Chemistry of Solid Surfaces, iChEM, Key Laboratory of Chemical Biology of Fujian Province, and College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, Fujian, 361005 China
Search for more papers by this authorCorresponding Author
Hai-Chao Xu
State Key Laboratory of Physical Chemistry of Solid Surfaces, iChEM, Key Laboratory of Chemical Biology of Fujian Province, and College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, Fujian, 361005 China
E-mail: [email protected]Search for more papers by this authorSummary of main observation and conclusion
An electrochemical synthesis of oxazol-2-ones and imidazol-2-ones has been developed via 5-exo-dig cyclization of propargylic carbamates- and ureas-derived amidyl radicals. The electrosynthesis relies on the dual function of 2,2,6,6-tetramethylpiperidin- 1-yl)oxyl (TEMPO) as a redox mediator for amidyl radical formation and an oxygen atom donor. The reactions are conducted under mild conditions using a simple setup and provide convenient access to functionalized oxazol-2-ones and imidazol-2-ones from readily available materials.
Supporting Information
| Filename | Description |
|---|---|
| cjoc201900500-sup-0001-SupInfo.pdfPDF document, 11.3 MB | Appendix S1: Supporting Information |
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