Unsupported Nanoporous Gold-Catalyzed Chemoselective Reduction of Quinolines Using Formic Acid as a Hydrogen Source

被引：9

作者：

Butt, Madiha ^{[1
]}

Zhao, Yuhui ^{[1
]}

Feng, Xiujuan ^{[1
]}

Lu, Ye ^{[1
,3
]}

Jin, Tienan ^{[2
]}

Yamamoto, Yoshinori ^{[1
,2
]}

Bao, Ming ^{[1
]}

机构：

[1] Dalian Univ Technol, State Key Lab Fine Chem, Dalian 116023, Peoples R China

[2] Tohoku Univ, Grad Sch Sci, Dept Chem, Sendai, Miyagi 9808577, Japan

[3] Inner Mongolia Univ Nationalities, Coll Chem & Chem Engn, NII, Inner Mongolia Key Lab Carbon Nanomat, Tongliao 028000, Peoples R China

来源：

CHEMISTRYSELECT | 2019年 / 4卷 / 21期

基金：

中国国家自然科学基金;

关键词：

AuNPore; quinoline; HCO2H; reduction; 1; 2; 3; 4-tetrahydroquinolines; ASYMMETRIC TRANSFER HYDROGENATION; HIGHLY ENANTIOSELECTIVE HYDROGENATION; N-HETEROAROMATIC COMPOUNDS; SELECTIVE HYDROGENATION; PALLADIUM NANOPARTICLES; HOMOGENEOUS HYDROGENATION; RUTHENIUM NANOPARTICLES; MILD CONDITIONS; VERSATILE; RHODIUM;

D O I：

10.1002/slct.201901309

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The unsupported nanoporous gold (AuNPore) is demonstrated to be an active and stable heterogeneous catalyst for chemoselective transfer hydrogenation of quinolines using bio-renewable formic acid (HCO2H) as hydrogen source. The AuNPore-catalyzed transfer hydrogenation of quinolines proceeded smoothly in the presence of low amounts of HCO2H at a relatively low temperature to produce the desired 1,2,3,4-tetrahydroquinolines (py-THQs) in good to excellent yields. Mechanistic studies revealed that the AuNPore-catalyzed transfer hydrogenation of quinolines proceeded through a sequence of 1,4-hydride addition, isomerization, and 1,2-hydride addition. This operationally simple protocol offers a practical alternative to the currently known methods for chemoselective quinoline reduction.

引用

页码：6572 / 6577

页数：6

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