Fukuyama Reduction and Integrated Thioesterification/Fukuyama Reduction of Thioesters and Acyl Chlorides Using Continuous Flow

被引：30

作者：

Asadi, Mousa ^{[1
]}

Bonke, Shannon ^{[1
]}

Poyzos, Anastasios ^{[2
]}

Lupton, David W. ^{[1
]}

机构：

[1] Monash Univ, Sch Chem, Clayton, Vic 3800, Australia

[2] CSIRO, Clayton, Vic 3800, Australia

来源：

ACS CATALYSIS | 2014年 / 4卷 / 06期

关键词：

Fukuyama reduction; heterogeneous catalysis; multistep continuous flow; thioesterification; catch-and-release; PALLADIUM NANOPARTICLES; ORGANIC-SYNTHESIS; ALDEHYDES; EFFICIENT; CHEMISTRY; ESTERS; MICROREACTORS; OXIDATION; CATALYST; REACTORS;

D O I：

10.1021/cs5004917

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

Fukuyama reduction of thioesters has been achieved using a polymer-supported Pd[O] catalyst (Pd/XAD-4), and continuous flow conditions. The generality of this reaction is good with a range of aldehydes prepared in excellent yields. In addition, an integrated multistep thioesterfication/Fukuyama reduction has been developed that allows acyl chlorides to be directly converted to the corresponding aldehydes. Integral to this process is the use of polymer-supported amine and isocyanate reagents to achieve thioesterification and scavenge unreacted thiol. In addition, catch-and-release purification has been employed to enable isolation of the aldehyde from silylthioether byproducts without the need for chromatographic purification.

引用

页码：2070 / 2074

页数：5

共 58 条

[21] Heterogeneous Catalytic Hydrogenation Reactions in Continuous-Flow Reactors [J].