Paper
Recent advances in synthetic transformations mediated by cerium(IV) ammonium nitrate.
Published Apr 20, 2004 · V. Nair, L. Balagopal, R. Rajan
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Abstract
Cerium(IV) ammonium nitrate (CAN) has recently emerged as a versatile reagent for oxidative electron transfer; the overwhelming number of reports serve as a testimony to the unparalleled utility of CAN in a variety of transformations of synthetic importance. Our recent work has uncovered novel carbon-carbon bond-forming reactions leading to the one-pot synthesis of dihydrofurans, tetrahydrofurans, and aminotetralins. In addition, we have developed a number of facile carbon-heteroatom bond-forming reactions by the CAN-mediated oxidative addition of soft anions to alkenes. A mechanistic rationale has been provided for the reactions explored. As might be expected of very powerful one-electron oxidants, the chemistry of cerium(IV) oxidation of organic molecules is dominated by radical and radical cation chemistry.
Cerium(IV) ammonium nitrate (CAN) offers versatile oxidative electron transfer for various synthetic transformations, including novel carbon-carbon bond-forming reactions and facile carbon-heteroatom bond-forming reactions.
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