Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 353, Issue 6, Pages 865-870Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201000906
Keywords
Baeyer-Villiger oxidation; organocatalysis; peroxides; pyrazinium salts; sulfoxidation
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Funding
- Czech Science Foundation [203/07/1246]
- Ministry of Education, Youth and Sports [LC03070]
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A series of 3-substituted pyrazinium tetrafluoroborates was prepared as simple analogues of flavinium salts which are efficient organocatalysts for oxidations with hydrogen peroxide. It was shown that pyrazinium derivatives with an electron-withdrawing substituent catalyze mild oxidations of sulfides to sulfoxides and Baeyer-Villiger oxidations in a similar way to flavinium catalysts. The most reactive catalyst, 3-cyanopyrazinium tetrafluoroborate, was efficiently employed in preparative sulfoxidations of aromatic and aliphatic sulfides as well as in Baeyer-Villiger oxidations of cyclobutanones. A proposed mechanism for the catalysis is based on the formation of pyrazine hydroperoxide which is the agent oxidizing the substrate.
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