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

Naohiro Fukuda; Minoru Izumi; Tomomi Ikemoto

doi:10.1016/j.tetlet.2015.04.115

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

Naohiro Fukuda, Minoru Izumi, Tomomi Ikemoto

Research output: Contribution to journal › Article › peer-review

8 Citations (Scopus)

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	https://doi.org/10.1016/j.tetlet.2015.04.115
Publication status	Published - May 30 2015

Keywords

Alcohol
Imide
NaOCl
Nitroxyl radical
Oxidation

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

Access to Document

10.1016/j.tetlet.2015.04.115

Cite this

@article{6134a18e34374700ab9016139fdc5a35,

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

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.",

keywords = "Alcohol, Imide, NaOCl, Nitroxyl radical, Oxidation",

author = "Naohiro Fukuda and Minoru Izumi and Tomomi Ikemoto",

year = "2015",

month = may,

day = "30",

doi = "10.1016/j.tetlet.2015.04.115",

language = "English",

volume = "56",

pages = "3905--3908",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Limited",

number = "25",

}

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 - 2015/5/30

Y1 - 2015/5/30

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 -

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

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this