Oxidative addition of 1,3-dicarbonyl compounds to alkenes mediated by cerium(IV) ammonium nitrate and manganese(III) acetate: a comparative study

Abstract

The oxidative addition of dimedone, acetylacetone and ethyl acetoacetate to cyclic and acyclic alkenes mediated by CAN gives dihydrofurans in good yields. Similar addition of the radical generated from dimethyl malonate to alkenes provides lactones. A comparative study of these reactions vis-à-vis those mediated by Mn(OAc)3 has shown that the former generally lead to higher yields of products. The milder reaction conditions, experimental simplicity, and the solubility of CAN in common organic solvents like methanol, acetonitrile and THF are other advantages. Thus it appears from this study that CAN is superior to the commonly used Mn(OAc)3.