Kharasch-Sosnovsky Oxidation

Kharasch-Sosnovsky Oxidation

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  • General Characteristics

Allylic C-H oxidation can be effected using acylperoxide under copper-catalyzed conditions. The alkene starting materials are usually used in excess. The terminal olefins are formed as major products.

  • General References


  • Reaction Mechanism

The proposed mechanisms starts with the formation of the oxyl radical species from acylperoxide and copper(I) (process known as the Fenton reaction), which then cleaves the allylic C-H bond.


  • Examples

The application to the synthesis of Taxol.[1]


An asymmetric version using a chiral ligand.[2]


  • Experimental Procedure

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  • References

[1] Mukaiyama, T. et al. Chem. Eur. J. 1999, 5, 121. [abstract]
[2] Gokhale, A. S.; Minidis, A. B. E.; Pfaltz, A. Tetrahedron Lett. 1995, 36, 1831. doi:10.1016/0040-4039(95)00140-8

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