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An organocatalyst N-hydroxyphthalimide (NHPI) forms the strongly oxidizing N-oxyl radical species (PINO) in the presence of appropriate oxidizing agents. This radical is highly active in abstracting a hydrogen from hydrocarbons.
This is a valuable catalytic system in which C(sp3)-H bonds can be oxidized under relatively mild conditions. Further developments, especially the improvement of regioselectivity, are awaited.
- Ishii, Y.; Nakayama, K.; Takeno, M.; Sakaguchi, S.; Iwahama, T.; Nishiyama, Y. J. Org. Chem. 1995, 60, 3934. DOI: 10.1021/jo00118a002
- Ishii, Y.; Sakaguchi, S.; Iwahama, T. Adv. Synth. Catal. 2001, 343, 393. [abstract]
- 石井康敬、[PDF] 誌 2001, 59, 2.
- Recupero, F.; Punta, C. Chem. Rev. 2007, 107, 3800. DOI: 10.1021/cr040170k
- Melone, L.; Punta, C. Beil. J. Org. Chem. 2013, 9, 1296. doi: 10.3762/bjoc.9.146
In recent years, the NHPI system has been extended to the direct fluorination and amination of sp3 C-H bonds.
N-Oxy Radical Chemistry (The Kanai Group at University of Tokyo, PDF)