Journal of Synthetic Organic Chemistry, Japan
Online ISSN : 1883-6526
Print ISSN : 0037-9980
ISSN-L : 0037-9980
Application of Cerium Reagents to Organic Synthesis
Koichiro OSHIMA
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1982 Volume 40 Issue 12 Pages 1171-1179

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Abstract
Synthetically useful reactions, especially oxidation and reduction, with cerium reagents are described. Topics in oxidation are (1) selective oxidation of secondary alcohols in the presence of primary ones, (2) oxidation of benzylic CH2 or CH3 group to carbonyl moiety, (3) conversion of hydroquinones to quinones, (4) oxidation of sulfur- and nitrogen-containing compounds, and (5) miscellaneous reactions.
Various new reduction methods with CeCl3-NaBH4 or Ce-I2 system are recently developed. These involves (1) selective 1, 2-reduction of α, β-unsaturated carbonyl compounds, (2) chemoselective reduction of ketones in the presence of aldehydes, and (3) reductive coupling of carbonyls with low valent cerium reagent.
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© The Society of Syhthetic Organic Chemistry, Japan
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