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- Title
Selective Aerobic Oxidation of Secondary C (sp3)-H Bonds with NHPI/CAN Catalytic System.
- Authors
Wang, Lingyao; Zhang, Yuanbin; Yuan, Haoran; Du, Renfeng; Yao, Jia; Li, Haoran
- Abstract
The direct aerobic oxidation of secondarty C(sp3)-H bonds was achieved in the presence of N-hydroxyphthalimide (NHPI) and cerium ammonium nitrate (CAN) under mild conditions. Various benzylic methylenes could be oxidized to carbonyl compounds in satisfied selectivity while saturated cyclic alkanes could be further oxidized to the corresponding lactones with the catalytic system. Remarkably, 25% of isochroman was converted to corresponding ketone with a selectivity of 96%. The reaction was initiated by hydrogen atom abstraction from NHPI by cerium and nitrates under oxygen atmosphere to form PINO radicals. 2,2,6,6-Tetramethylpiperidine-1-oxyl (TEMPO) addition experiments showed that the oxidation proceeded via a complex radical chain mechanism and an ion pathway.
- Subjects
ABSTRACTION reactions; AMMONIUM nitrate; OXIDATION; SELECTIVE catalytic oxidation; CARBONYL compounds; CERIUM
- Publication
Catalysis Letters, 2021, Vol 151, Issue 6, p1663
- ISSN
1011-372X
- Publication type
Article
- DOI
10.1007/s10562-020-03406-6