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Electrochemically Tuned Oxidative [4+2] Annulation and Dioxygenation of Olefins with Hydroxamic Acids
- Source :
- Angewandte Chemie. 133:3219-3225
- Publication Year :
- 2020
- Publisher :
- Wiley, 2020.
-
Abstract
- This work represents the first [4+2] annulation of hydroxamic acids with olefins for the synthesis of benzo[c][1,2]oxazines scaffold via anode-selective electrochemical oxidation. This protocol features mild conditions, is oxidant free, shows high regioselectivity and stereoselectivity, broad substrate scope of both alkenes and hydroxamic acids, and is compatible with terpenes, peptides, and steroids. Significantly, the dioxygenation of olefins employing hydroxamic acid is also successfully achieved by switching the anode material under the same reaction conditions. The study not only reveals a new reactivity of hydroxamic acids and its first application in electrosynthesis but also provides a successful example of anode material-tuned product selectivity.
- Subjects :
- Annulation
Hydroxamic acid
010405 organic chemistry
Regioselectivity
Substrate (chemistry)
General Chemistry
General Medicine
010402 general chemistry
Electrosynthesis
01 natural sciences
Combinatorial chemistry
Catalysis
0104 chemical sciences
chemistry.chemical_compound
chemistry
Stereoselectivity
Reactivity (chemistry)
Selectivity
Subjects
Details
- ISSN :
- 15213757 and 00448249
- Volume :
- 133
- Database :
- OpenAIRE
- Journal :
- Angewandte Chemie
- Accession number :
- edsair.doi.dedup.....26778c947cffc0870ca23dfac2fda947