Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 22, Issue 40, Pages 14141-14146Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201602597
Keywords
hydrazones; nitrogen radicals; oximes; oxygen radicals; photocatalysis
Categories
Funding
- NSFC [21272087, 21472058, 21232003]
- Youth Chen-Guang Project of Wuhan [2015070404010180]
- CCNU [CCNU15A02009, 2015YBZD011]
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A cooperative TEMPO and photoredox catalytic strategy was applied for the first time to the direct conversion of N-H and O-H bonds into N-and O-centred radicals, enabling a general and selective oxidative radical oxyamination and dioxygenation of various beta,gamma-unsaturated hydrazones and oximes. In the reaction, O-2 was employed not only as a terminal oxidant but also as the oxygen source. This protocol provided efficient access to the synthesis of various synthetically and biologically important pyrazoline, pyridazine and isoxazoline derivatives under metal-free and mild reaction conditions. Mechanistic studies revealed that the cooperative organophotocatalytic system functions through two single-electron-transfer (SET) processes.
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