Recent advances in synthetic transformations mediated by cerium(IV) ammonium nitrate.
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.
Nair
Vijay
V
Organic Chemistry Division, Regional Research Laboratory (CSIR), Trivandrum 695 019, India. gvn@csrrltrd.ren.nic.in
Balagopal
Lakshmi
L
Rajan
Roshini
R
Mathew
Jessy
J
D002563:Cerium / Q000737:chemistry*; D004579:Electron Transport; D005663:Furans / Q000138:chemical synthesis / Q000737:chemistry; D008956:Models, Chemical; D010084:Oxidation-Reduction; D013237:Stereoisomerism; D013764:Tetrahydronaphthalenes / Q000138:chemical synthesis / Q000737:chemistry
D005663:Furans; D013764:Tetrahydronaphthalenes; D002563:Cerium; C004653:ceric ammonium nitrate