Cyclotrimetaphosphate-assisted ruthenium catalyst for the hydration of nitriles and oxidation of primary amines to amides under aerobic conditions in water

被引:4
|
作者
Chouhan, Kishor Kumar [1 ]
Chowdhury, Deep [1 ]
Mukherjee, Arup [1 ]
机构
[1] Indian Inst Technol Bhilai, Dept Chem, GEC Campus, Raipur 492015, Chhattisgarh, India
关键词
SALTS SYNTHESIS; ALCOHOLS; COMPLEXES; EFFICIENT; ACID; BOND; OXYGENATION; CHEMISTRY; LIGANDS; GOLD;
D O I
10.1039/d3ob00062a
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Amide bonds are ubiquitous and regarded as an essential constituent of many biologically active drug molecules and fine chemicals. We report a practical and operationally simple ruthenium-based catalytic system for the hydration of nitriles and aerobic oxidation of primary amines to the corresponding amides. Both reactions proceed without any external oxidant in water under aerobic conditions and exhibit a broad substrate scope. The mechanistic investigation was executed with the aid of control experiments and kinetic and spectroscopic studies of the reaction mixture.
引用
收藏
页码:2429 / 2439
页数:11
相关论文
共 33 条
  • [21] Copper-Catalyzed Aerobic Oxidation of Amines to Imines under Neat Conditions with Low Catalyst Loading
    Patil, Rajendra D.
    Adimurthy, Subbarayappa
    ADVANCED SYNTHESIS & CATALYSIS, 2011, 353 (10) : 1695 - 1700
  • [22] Catalyst-free aerobic oxidation of aldehydes into acids in water under mild conditions
    Zhang, Yue
    Cheng, Yujia
    Cai, Huizhuo
    He, Shaopo
    Shan, Qiheng
    Zhao, Hongwei
    Chen, Yiping
    Wang, Bo
    GREEN CHEMISTRY, 2017, 19 (23) : 5708 - 5713
  • [23] Use of Vitamin B12 as a Nontoxic and Natural Catalyst for the Synthesis of Benzoxazoles via Catechols and Primary Amines in Water under Aerobic Oxidation
    Sharghi, Hashem
    Hosseini, Mina Aali
    Aboonajmi, Jasem
    Aberi, Mahdi
    ACS SUSTAINABLE CHEMISTRY & ENGINEERING, 2021, 9 (33) : 11163 - 11170
  • [24] Selective Hydrogenation of Nitriles to Primary Amines Catalyzed by a Polysilane/SiO2-Supported Palladium Catalyst under Continuous-Flow Conditions
    Saito, Yuki
    Ishitani, Haruro
    Ueno, Masaharu
    Kobayashi, Shu
    CHEMISTRYOPEN, 2017, 6 (02): : 211 - 215
  • [25] RuCl3-DCHA CATALYST SYSTEM: A SELECTIVE AEROBIC OXIDATION OF PRIMARY BENZYLIC ALCOHOLS UNDER MILD CONDITIONS
    Yu, Kaihui
    Ye, Dongnai
    Shu, Lei
    Zhang, Shiyong
    Hu, Qiaosheng
    Liu, Liangxian
    SYNTHETIC COMMUNICATIONS, 2012, 42 (15) : 2318 - 2326
  • [26] Ruthenium-catalyzed oxidative decyanative cross-coupling of acetonitriles with amines in air: a general access to primary to tertiary amides under mild conditions
    Wang, Yuguang
    Wu, Zhongli
    Li, Qin
    Zhu, Bingchun
    Yu, Lei
    CATALYSIS SCIENCE & TECHNOLOGY, 2017, 7 (17) : 3747 - 3757
  • [27] A heterobimetallic rhodium(I)-ruthenium(II) catalyst for the Oppenauer-type oxidation of primary and secondary alcohols under mild conditions
    Gauthier, S
    Scopelliti, R
    Severin, K
    ORGANOMETALLICS, 2004, 23 (16) : 3769 - 3771
  • [28] Photocatalytic organic transformation by layered double hydroxides: highly efficient and selective oxidation of primary aromatic amines to their imines under ambient aerobic conditions
    Yang, Xiu-Jie
    Chen, Bin
    Li, Xu-Bing
    Zheng, Li-Qiang
    Wu, Li-Zhu
    Tung, Chen-Ho
    CHEMICAL COMMUNICATIONS, 2014, 50 (50) : 6664 - 6667
  • [29] Dehydration of primary amides to nitriles in water. Late-stage functionalization and 1-pot multistep chemoenzymatic processes under micellar catalysis conditions
    Wood, Alex B.
    Kincaid, Joseph R. A.
    Lipshutz, Bruce H.
    GREEN CHEMISTRY, 2022, 24 (07) : 2853 - 2858
  • [30] Recyclable gold nanoparticle catalyst for the aerobic alcohol oxidation and C-C bond forming reaction between primary alcohols and ketones under ambient conditions
    Kim, Sungjin
    Bae, Sang Won
    Lee, Jae Sung
    Park, Jaiwook
    TETRAHEDRON, 2009, 65 (07) : 1461 - 1466