Homogenous nickel-catalyzed chemoselective transfer hydrogenation of functionalized nitroarenes with ammonia-borane

被引：14

作者：

Dewangan, Chitrarekha ^{[1
]}

Kumawat, Sandeep ^{[1
]}

Bhatt, Tarun ^{[1
]}

Natte, Kishore ^{[1
]}

机构：

[1] Indian Inst Technol Hyderabad, Dept Chem, Sangareddy 502285, Telangana, India

来源：

CHEMICAL COMMUNICATIONS | 2023年 / 59卷 / 99期

关键词：

SELECTIVE HYDROGENATION; NITRO-COMPOUNDS; REDUCTION;

D O I：

10.1039/d3cc05173k

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Homogeneous Ni-catalyzed highly selective transfer hydrogenation of nitroarenes was successfully established using NH3BH3 as a hydrogen source. A broad range of functional groups were selectively reduced to provide the corresponding anilines in good to high yields. Further, pharmaceutically active compounds can be prepared that would otherwise be challenging to access. Homogeneous Ni-catalyzed highly chemoselective transfer hydrogenation of functionalized nitroarenes was successfully established using ammonia-borane as a hydrogen source.

引用

页码：14709 / 14712

页数：4

共 36 条

[21] Recent Developments in the Reduction of Aromatic and Aliphatic Nitro Compounds to Amines [J].

Orlandi, Manuel ;

Brenna, Davide ;

Harms, Reentje ;

Jost, Sonja ;

Benaglia, Maurizio .

ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2018, 22 (04) :430-445

[22] Seven-Step Continuous Flow Synthesis of Linezolid Without Intermediate Purification [J].

Russell, M. Grace ;

Jamison, Timothy F. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (23) :7678-7681

[23] From Hydrogenation to Transfer Hydrogenation to Hydrogen Auto-Transfer in Enantioselective Metal-Catalyzed Carbonyl Reductive Coupling: Past, Present, and Future [J].

Santana, Catherine Gazolla ;

Krische, Michael J. .

ACS CATALYSIS, 2021, 11 (09) :5572-5585

[24] Simple RuCl3-catalyzed N-Methylation of Amines and Transfer Hydrogenation of Nitroarenes using Methanol [J].

Sarki, Naina ;

Goyal, Vishakha ;

Tyagi, Nitin Kumar ;

Puttaswamy ;

Narani, Anand ;

Ray, Anjan ;

Natte, Kishore .

CHEMCATCHEM, 2021, 13 (07) :1722-1729

[25] A Reusable Co Catalyst for the Selective Hydrogenation of Functionalized Nitroarenes and the Direct Synthesis of Imines and Benzimidazoles from Nitroarenes and Aldehydes [J].

Schwob, Tobias ;

Kempe, Rhett .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (48) :15175-15179

[26] Maximizing hydrogen utilization efficiency in tandem hydrogenation of nitroarenes with ammonia borane [J].

Shen, Mengqi ;

Bendel, Christoph ;

Vibbert, Hunter B. B. ;

Khine, Pan Thi ;

Norton, Jack R. R. ;

Moment, Aaron J. J. .

GREEN CHEMISTRY, 2023, 25 (18) :7183-7188

[27] Room-Temperature Chemoselective Reduction of 3-Nitrostyrene to 3-Vinylaniline by Ammonia Borane over Cu Nanoparticles [J].

Shen, Mengqi ;

Liu, Hu ;

Yu, Chao ;

Yin, Zhouyan ;

Muzzio, Michelle ;

Li, Junrui ;

Xi, Zheng ;

Yu, Yongsheng ;

Sun, Shouheng .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2018, 140 (48) :16460-16463

[28] Highly Active and Chemoselective Reduction of Halogenated Nitroarenes Catalyzed by Ordered Mesoporous Carbon Supported Platinum Nanoparticles [J].

Sheng, Yao ;

Wang, Xueguang ;

Xing, Zhikang ;

Chen, Xiubin ;

Zou, Xiujing ;

Lu, Xionggang .

ACS SUSTAINABLE CHEMISTRY & ENGINEERING, 2019, 7 (09) :8908-8916

[29]

Tasker SZ, 2014, NATURE, V509, P299, DOI 10.1038/nature13274

[30]

Vardanyan RS, 2006, SYNTHESIS OF ESSENTIAL DRUGS, P9, DOI 10.1016/B978-044452166-8/50002-9

← 1 2 3 4 →