Safe and Selective Nitro Group Reductions Catalyzed by Sustainable and Recyclable Fe/ppm Pd Nanoparticles in Water at Room Temperature

被引：143

作者：

Feng, Jie ^{[1
,2
]}

Handa, Sachin ^{[1
]}

Gallou, Fabrice ^{[3
]}

Lipshutz, Bruce H. ^{[1
]}

机构：

[1] Univ Calif Santa Barbara, Dept Chem & Biochem, Santa Barbara, CA 93106 USA

[2] Nanjing Univ Sci & Technol, Coll Chem Engn, Nanjing 210094, Jiangsu, Peoples R China

[3] Novartis Pharmaceut, Basel, Switzerland

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2016年 / 55卷 / 31期

关键词：

green chemistry; micelles; nanoparticles; reduction; water chemistry; CROSS-COUPLINGS; PALLADIUM-NANOPARTICLE; AROMATIC-AMINES; NITROARENES; HYDROGENATION; COMPLEXES; EFFICIENT; ANILINES; DESIGN; ETHERS;

D O I：

10.1002/anie.201604026

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

As a result of a unique synergy between ligand-free Fe/ppm Pd nanoparticles and PEG-containing designer surfactants, a facile and selective reduction of nitro-containing aromatics and heteroaromatics can be effected in water at room temperature in the presence of NaBH4. This new nanotechnology involves low catalyst loadings, is highly chemoselective, and tolerates a wide variety of functional groups. The process, which includes recycling of the entire aqueous medium, offers a general, environmentally responsible, and notably safe approach to highly valued reductions of nitro-containing compounds.

引用

页码：8979 / 8983

页数：5

共 55 条

[11] Surfactant-free hydrothermal synthesis of sub-10 nm γ-Fe2O3-polymer porous composites with high catalytic activity for reduction of nitroarenes [J].

Gu, Xianmo ;

Sun, Zhenhua ;

Wu, Shuchang ;

Qi, Wei ;

Wang, Haihua ;

Xu, Xianzhu ;

Su, Dangsheng .

CHEMICAL COMMUNICATIONS, 2013, 49 (86) :10088-10090

[12] Sustainable Fe-ppm Pd nanoparticle catalysis of Suzuki-Miyaura cross-couplings in water [J].

Handa, Sachin ;

Wang, Ye ;

Gallou, Fabrice ;

Lipshutz, Bruce H. .

SCIENCE, 2015, 349 (6252) :1087-1091

[13]

Hartwig J.F., 1998, ANGEW CHEM INT EDIT, V110, P2154

[14]

Hartwig JF, 1998, ANGEW CHEM INT EDIT, V37, P2046, DOI 10.1002/(SICI)1521-3773(19980817)37:15<2046::AID-ANIE2046>3.0.CO

[15]

2-L

[16] Carbon-heteroatom bond-forming reductive eliminations of amines, ethers, and sulfides [J].

Hartwig, JF .

ACCOUNTS OF CHEMICAL RESEARCH, 1998, 31 (12) :852-860

[17] Efficient Catalytic System for Chemoselective Hydrogenation of Halonitrobenzene to Haloaniline Using PtZn Intermetallic Compound [J].

Iihama, Sho ;

Furukawa, Shinya ;

Komatsu, Takayuki .

ACS CATALYSIS, 2016, 6 (02) :742-746

[18] Nitrogen-Doped Graphene-Activated Iron-Oxide-Based Nanocatalysts for Selective Transfer Hydrogenation of Nitroarenes [J].

Jagadeesh, Rajenahally V. ;

Natte, Kishore ;

Junge, Henrik ;

Beller, Matthias .

ACS CATALYSIS, 2015, 5 (03) :1526-1529

[19] Nanoscale Fe2O3-Based Catalysts for Selective Hydrogenation of Nitroarenes to Anilines [J].

Jagadeesh, Rajenahally V. ;

Surkus, Annette-Enrica ;

Junge, Henrik ;

Pohl, Marga-Martina ;

Radnik, Joerg ;

Rabeah, Jabor ;

Huan, Heming ;

Schuenemann, Volker ;

Brueckner, Angelika ;

Beller, Matthias .

SCIENCE, 2013, 342 (6162) :1073-1076

[20] Efficient and highly selective iron-catalyzed reduction of nitroarenes [J].

Jagadeesh, Rajenahally V. ;

Wienhoefer, Gerrit ;

Westerhaus, Felix A. ;

Surkus, Annette-Enrica ;

Pohl, Marga-Martina ;

Junge, Henrik ;

Junge, Kathrin ;

Beller, Matthias .

CHEMICAL COMMUNICATIONS, 2011, 47 (39) :10972-10974

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