期刊
SCIENCE CHINA-CHEMISTRY
卷 64, 期 5, 页码 753-760出版社
SCIENCE PRESS
DOI: 10.1007/s11426-020-9958-6
关键词
photocatalytic-controlled reaction; proton-coupled electron transfer; ring opening; recyclization process; rearrangement; aerobic oxidation; the Ladenburg rearrangement; pyridinium
资金
- National Natural Science Foundation of China [22061003, 21861006]
- Guangxi Natural Science Foundation of China [2016GXNSFEA380001, 2019GXNSFAA245027]
- Guangxi Key RD Program [AB18221005]
- Science and Technology Major Project of Guangxi [AA17204058-21]
- Guangxi Science and Technology Base and Special Talents [guike AD19110027]
This study presents two methods for the selective oxidation of pyridiniums, one utilizing photocatalysis and the other visible light induction. The transformations involve oxygen-mediated cycloaddition, PCET, pyridine ring opening, and recyclization to convert pyridiniums to pyrroles, and free radical rearrangement/aerobic oxidation catalyzed by cobalt (II) for the selective formation of 4-carbonyl pyridines.
This study proposes two different methods of photocatalytic-controlled and visible light-induced selective oxidation of pyridiniums with air as the terminal oxidant. The key to these transformations is to choose the appropriate light source and photocatalyst. Pyridiniums are successfully converted into pyrroles through oxygen-mediated cycloaddition, proton-coupled electron transfer (PCET), pyridine ring opening, and recyclization. The other route is that pyridiniums selectively form 4-carbonyl pyridines through free radical rearrangement/aerobic oxidation under the catalysis of cobalt (II).
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