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

被引：13

作者：

Fukuda, Naohiro ^{[1
]}

Izumi, Minoru ^{[2
]}

Ikemoto, Tomomi ^{[1
]}

机构：

[1] Takeda Pharmaceut Co Ltd, CMC Ctr, Chem Dev Labs, Yodogawa Ku, Osaka 5328686, Japan

[2] Okayama Univ, Grad Sch Environm & Life Sci, Kita Ku, Okayama 7008530, Japan

来源：

TETRAHEDRON LETTERS | 2015年 / 56卷 / 25期

关键词：

Oxidation; Alcohol; NaOCl; Nitroxyl radical; Imide; OPPENAUER-TYPE OXIDATION; TRANSITION-METAL-FREE; AEROBIC OXIDATION; SELECTIVE OXIDATION; SECONDARY ALCOHOLS; MECHANISTIC INVESTIGATIONS; MILD CONDITIONS; KETONES; EFFICIENT; TEMPO;

D O I：

10.1016/j.tetlet.2015.04.115

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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. (C) 2015 Elsevier Ltd. All rights reserved.

引用

页码：3905 / 3908

页数：4

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