Corey–Kim oxidation
Corey-Kim oxidation | |
---|---|
Named after | Elias James Corey Choung Un Kim |
Reaction type | Organic redox reaction |
Identifiers | |
Organic Chemistry Portal | corey-kim-oxidation |
The Corey–Kim oxidation is an
Although the Corey–Kim oxidation possesses the distinctive advantage over Swern oxidation of allowing an operation above –25 °C, it is not so commonly used due to issues with selectivity in substrates susceptible to chlorination by N-chlorosuccinimide.
Reaction mechanism
Dimethyl sulfide (Me2S) is treated with N-chlorosuccinimide (NCS), resulting in formation of an "active DMSO" species that is used for the activation of the alcohol. Addition of triethylamine to the activated alcohol leads to its oxidation to aldehyde or ketone and generation of dimethyl sulfide. In variance with other alcohol oxidation using "activated DMSO," the reactive oxidizing species is not generated by reaction of DMSO with an electrophile. Rather, it is formed by oxidation of dimethyl sulfide with an oxidant (NCS).
Under Corey–Kim conditions
Variations
Substituting dimethyl sulfide with something less noxious has been the goal of several research projects. Ohsugia et al.[6] substituted a long-chain sulfide, dodecyl methyl sulfide, for dimethyl sulfide. Crich et al.[7] utilized fluorous technology in a similar manner.
See also
References
- .
- .
- .
- .
- .
- ^ Ohsugia, S.-I.; Nishidea, K.; Oonob, K.; Okuyamab, K.; Fudesakaa, M.; Kodamaa, S.; Node, M. Tetrahedron 2003, 59, 8393–8398.
- ^ Crich, D.; Neelamkavil, S. Tetrahedron 2002, 58, 3865–3870.