Journal
ASIAN JOURNAL OF ORGANIC CHEMISTRY
Volume 10, Issue 11, Pages 2907-2910Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ajoc.202100575
Keywords
alkene; styrene; chloroamidation; oxidation; oxone
Categories
Funding
- JSPS.KAKENHI [20K20559, 15H05484, 18H01973]
- Takahashi Industrial and Economic Research Foundation
- Society of Iodine Science
- Nagoya University Graduate Program of Transformative Chem-Bio Research
- Grants-in-Aid for Scientific Research [15H05484, 18H01973, 20K20559] Funding Source: KAKEN
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The reported method is a practical and environmentally friendly approach for the oxidative Ritter-type chloroamidation of alkenes using sodium chloride and oxone in acetonitrile under mild conditions. The reaction shows excellent chemoselectivity and can be easily scaled up for synthesis. No catalyst is needed for this non-aqueous reaction.
We report a practical and environmentally benign method for the oxidative Ritter-type chloroamidation of alkenes using sodium chloride and oxone as a chlorinating source and an oxidant, respectively, in acetonitrile under mild conditions. The reaction proceeded smoothly under non-aqueous conditions without the use of any catalyst. Excellent chemoselectivity (i. e., chloroamidation versus dichlorination) could be achieved for electron-deficient styrenes. In addition, this protocol could be easily applied to 7-gram-scale synthesis.
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