Chemoselective Metal-Free Aerobic Alcohol Oxidation in Lignin

被引：563

作者：

Rahimi, Alireza ^{[1
]}

Azarpira, Ali ^{[2
,3
]}

Kim, Hoon ^{[2
,3
]}

Ralph, John ^{[2
,3
]}

Stahl, Shannon S. ^{[1
]}

机构：

[1] Univ Wisconsin, Dept Chem, Madison, WI 53706 USA

[2] Wisconsin Energy Inst, Dept Biochem, Madison, WI 53726 USA

[3] Wisconsin Energy Inst, DOE Great Lakes Bioenergy Res Ctr, Madison, WI 53726 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2013年 / 135卷 / 17期

基金：

美国国家科学基金会;

关键词：

ALKALINE HYDROGEN-PEROXIDE; O BOND-CLEAVAGE; CATALYZED OXIDATION; HIGHLY EFFICIENT; NITRIC-ACID; C-C; ALDEHYDES; DEGRADATION; MECHANISM; MODELS;

D O I：

10.1021/ja401793n

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An efficient organocatalytic method for chemoselective aerobic oxidation of: secondary benzylic alcohols within lignin model compounds has been identified. Extension to selective oxidation in natural lignins has also been demonstrated. The optimal catalyst system consists of 4-acetamido-TEMPO (5 mol %; TEMPO = 2,2,6,6-tetramethylpiperidine-N-oxyl) in combination with HNO3 and HCl (10 mol % each). Preliminary studies highlight the prospect of combining this method with a subsequent oxidation step to achieve C-C bond cleavage.

引用

页码：6415 / 6418

页数：4

共 51 条

[1] Acid-Catalyzed Decomposition of the Benzyl Nitrite Intermediate in HNO3-Mediated Aerobic Oxidation of Benzyl Alcohol [J].