Continuous-Flow Aerobic Oxidation of Primary Alcohols with a Copper(I)/TEMPO Catalyst

被引：101

作者：

Greene, Jodie F. ^{[1
]}

Hoover, Jessica M. ^{[1
]}

Mannel, David S. ^{[2
]}

Root, Thatcher W. ^{[2
]}

Stahl, Shannon S. ^{[1
]}

机构：

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

[2] Univ Wisconsin, Dept Chem & Biol Engn, Madison, WI 53706 USA

来源：

ORGANIC PROCESS RESEARCH & DEVELOPMENT | 2013年 / 17卷 / 10期

基金：

美国国家科学基金会;

关键词：

SELECTIVE OXIDATION; ALDEHYDES; TEMPO; INTENSIFICATION; MECHANISM; KETONES; BENIGN; BLEACH; OXYGEN;

D O I：

10.1021/op400207f

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

A scalable, continuous-flow process has been developed to implement a homogeneous Cu-I/TEMPO catalyst system for aerobic oxidation of primary alcohols to aldehydes. This catalyst system is compatible with a wide range of alcohols bearing diverse functional groups. A dilute oxygen source (9% O-2 in N-2) is used to avoid flammable oxygen/organic mixtures. Residence times in the heated reaction zone can be as low as 5 min with activated (e.g., benzylic) alcohols. The method has been demonstrated with nine different alcohols, including one up to 100 g scale. This flow-based catalytic method exhibits significant advantages for aerobic oxidation of alcohols, including substantially shorter residence times and broader substrate scope relative to a Pd-catalyzed method that we reported recently.

引用

页码：1247 / 1251

页数：5

共 35 条

[1] Intensification of TEMPO-mediated aerobic alcohol oxidations under three-phase flow conditions [J].