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Synlett 1999; 1999(6): 834
DOI: 10.1055/s-1999-6186
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Ceric(IV) Ammonium Nitrate

Thomas Sommermann*
  • *Institut für Organische Chemie, Universität Stuttgart, Pfaffenwaldring 55, D-70569 Stuttgart, Germany
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Publication Date:
31 December 1999 (online)

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Among lanthanide reagents, ceric(IV) ammonium nitrate (CAN), CeIV(NH4)2(NO3)6, is the most notable oxidant and has been utilized extensively for a broad variety of oxidative transformations in organic chemistry. Recent studies have revealed protocols for mild conditions, fast conversions and convenient working-up procedures, and, in addition to the electron transfer capability, Lewis acid properties extend the scope of transformations. The oxidation of various functional groups and especially unsaturated systems with CAN is well established and was reviewed some years ago. In transition metal mediated radical additions of CH-acidic compounds to olefins, CAN turned out to be superior to Mn(OAc)3 in many respects, especially when mild and non-acidic conditions are required. Furthermore, the reagent offers selective methods of introducing and removing various protecting groups via electron transfer or Lewis acid catalysis.