US EPA

3737684 

Journal Article 

Review 

Cerium(IV) ammonium nitrate as a catalyst in organic synthesis 

Sridharan, V; Menéndez, JC 

2010 

Yes 

Chemical Reviews
ISSN: 0009-2665
EISSN: 1520-6890 

110 

6 

3805-3849 

English 

20359233 

10.1021/cr100004p 

WOS:000278719900012 

Cerium has ability to participate in one-electron transfer reactions and to exist in two stable, adjacent oxidation states +3 and +4 with configurations [Xe]4f1 and [Xe]4f0,respectively. The high reduction potential of Ce(IV) makes Ce(IV) a very efficient oxidizing reagent as compared to other cations. The cerium(IV) ammonium nitrate (CAN) is an excellent reagent for the oxidation of benzylic alcohols and cyclopropylcarbinols to the corresponding carbonyl compounds, but gives cleavage products when applied to other types of substrates such as 1,2-diarylethanols and bicyclo[2.2.1]heptan-2- ol derivatives. The association of CAN, in catalytic amounts, and N-bromosuccinimide (NBS) provides an efficient reagent for the direct transformation of aryl epoxides into α-hydroxyarylketones, although the reaction failed for alkyl and cyclic epoxides. CAN is a good initiator for the direct transformation of diethyl malonate into diethyl ketomalonate by molecular oxygen.