Safe and convenient nitroxyl radical and imide dual catalyzed NaOCl oxidation of alcohols to aldehydes/ketones

[Display omitted] A novel and practical oxidation of alcohols to carbonyl compounds using NaOCl in the presence of catalytic amounts of imide compound and nitroxyl radical has been developed. A wide variety of aliphatic, benzylic primary alcohols, and secondary alcohols were oxidized to afford the c...

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Bibliographic Details
Published inTetrahedron letters Vol. 56; no. 25; pp. 3905 - 3908
Main Authors Fukuda, Naohiro, Izumi, Minoru, Ikemoto, Tomomi
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 17.06.2015
Elsevier
Subjects
Alcohol
Chemistry
Chemistry, Organic
Imide
NaOCl
Nitroxyl radical
Oxidation
Physical Sciences
Science & Technology
Imide
Alcohol
Oxidation
Nitroxyl radical
NaOCl
MECHANISTIC INVESTIGATIONS
SELECTIVE OXIDATION
OPPENAUER-TYPE OXIDATION
SECONDARY ALCOHOLS
KETONES
MILD CONDITIONS
AEROBIC OXIDATION
TEMPO
EFFICIENT
TRANSITION-METAL-FREE
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Summary:[Display omitted] A novel and practical oxidation of alcohols to carbonyl compounds using NaOCl in the presence of catalytic amounts of imide compound and nitroxyl radical has been developed. A wide variety of aliphatic, benzylic primary alcohols, and secondary alcohols were oxidized to afford the corresponding aldehydes and ketones in up to 98% yield without undesired halogenation on aromatic rings or double bonds. The oxidation safely proceeded not only in the presence of K2CO3 but also by a slow addition of NaOCl without tedious pH adjustment.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2015.04.115