Studies on Iron-Catalyzed Aerobic Oxidation of Benzylic Alcohols to Carboxylic Acids

被引：22

作者：

Jiang, Xingguo ^{[1
,2
]}

Ma, Shengming ^{[1
,3
]}

机构：

[1] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, 345 Lingling Lu, Shanghai 200032, Peoples R China

[2] Univ Chinese Acad Sci, Beijing 100049, Peoples R China

[3] Fudan Univ, Dept Chem, 220 Handan Lu, Shanghai 200433, Peoples R China

来源：

SYNTHESIS-STUTTGART | 2018年 / 50卷 / 08期

关键词：

iron catalysis; aerobic oxidation; benzylic alcohols; carboxylic acids; electronic effects; steric effects; 2,5-FURANDICARBOXYLIC ACID; METAL-FREE; POTASSIUM-PERMANGANATE; SELECTIVE OXIDATION; ARYLBORONIC ACIDS; MOLECULAR-OXYGEN; SUZUKI-MIYAURA; ARYL BROMIDES; EFFICIENT; WATER;

D O I：

10.1055/s-0036-1591761

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A comprehensive study on aerobic oxidation of benzylic alcohols to carboxylic acids with a catalytic amount each of Fe(NO3) (3)<bold></bold>9H(2) O, TEMPO, and KCl is conducted. Various synthetically useful functional groups are well tolerated in the reaction. Distinct electronic and steric effects are observed in the reaction: electron-withdrawing groups accelerate the reaction while electron-donating groups make the reaction slower, and ortho -substituted substrates react slower than meta -substituted substrates. Several large-scale reactions (100 mmol) are conducted using a slow air flow of 30 mL/min to demonstrate the practicality of this method in an academic laboratory.

引用

页码：1629 / 1639

页数：11

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