Carbon-carbon bond forming reactions mediated by cerium(IV) reagents

Abstract

Organic synthesis using carbon centred radicals generated by one electron oxidants is of current interest. Although Mn(OAc)₃ has received the most attention, it appears that cerium(IV) ammonium nitrate (CAN) would be a very useful reagent for the generation of radicals. The recent application of CAN in the construction of C-C bonds are highlighted in this review. CAN has been shown to mediate the facile oxidative addition of 1,3-dicarbonyl compounds to activated and unactivated alkenes leading to dihydrofurans and furanones. In most cases the reactions occur under milder conditions and the yields are superior when compared to Mn(OAc)₃ mediated reactions. The results available thus far suggest that CAN offers cast potential in radical mediated organic synthesis.