Abstract
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.
| Original language | English |
|---|---|
| Pages (from-to) | 3905-3908 |
| Number of pages | 4 |
| Journal | Tetrahedron Letters |
| Volume | 56 |
| Issue number | 25 |
| DOIs | |
| Publication status | Published - Mar 19 2015 |
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Keywords
- Alcohol
- Imide
- NaOCl
- Nitroxyl radical
- Oxidation
ASJC Scopus subject areas
- Biochemistry
- Organic Chemistry
- Drug Discovery
Cite this
Safe and convenient nitroxyl radical and imide dual catalyzed NaOCl oxidation of alcohols to aldehydes/ketones. / Fukuda, Naohiro; Izumi, Minoru; Ikemoto, Tomomi.
In: Tetrahedron Letters, Vol. 56, No. 25, 19.03.2015, p. 3905-3908.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Safe and convenient nitroxyl radical and imide dual catalyzed NaOCl oxidation of alcohols to aldehydes/ketones
AU - Fukuda, Naohiro
AU - Izumi, Minoru
AU - Ikemoto, Tomomi
PY - 2015/3/19
Y1 - 2015/3/19
N2 - 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.
AB - 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.
KW - Alcohol
KW - Imide
KW - NaOCl
KW - Nitroxyl radical
KW - Oxidation
UR - http://www.scopus.com/inward/record.url?scp=84930183176&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=84930183176&partnerID=8YFLogxK
U2 - 10.1016/j.tetlet.2015.04.115
DO - 10.1016/j.tetlet.2015.04.115
M3 - Article
AN - SCOPUS:84930183176
VL - 56
SP - 3905
EP - 3908
JO - Tetrahedron Letters
JF - Tetrahedron Letters
SN - 0040-4039
IS - 25
ER -