An Effective Catalytic Epoxidation of Terpenes with Hydrogen Peroxide under Organic Solvent-Free Conditions

作者：Kon Yoshihiro; Ono Yutaka; Matsumoto Tomohiro; Sato Kazuhiko^*

来源：Synlett, 2009, 2009(7): 1095-1098.

DOI：10.1055/s-0028-1088156

• oxidations
• catalysis
• epoxides
• terpenoids
• green chemistry

A catalytic system that operates well for the epoxidation of alpha-pinene, a very challenging Substrate, at near-neutral pH and ambient temperature without organic solvent was developed. With hydrogen peroxide as a terminal oxidant, combination of Na(2)WO(4), PhP(O)(OH)(2), and [Me(n-C(8)H(17))(3)N]HSO(4) successfully catalyzed the epoxidation of alpha-pinene to give a-pinene oxide in 95% selectivity at 91% conversion, while the previously published conditions that use NH(2)CH(2)P(O)(OH)(2) as a promoter provide no epoxide. The method is also well applicable to the epoxidation of the other acid-sensitive terpenes.

• 出版日期2009-4-23