Graphene Oxide as a Metal-free Carbocatalyst for Direct Amide Synthesis from Carboxylic Acid and Amine Under Solvent-Free Reaction Condition

被引:9
作者
Patel, Khushbu P. [1 ]
Gayakwad, Eknath M. [1 ]
Shankarling, Ganapati S. [1 ]
机构
[1] Inst Chem Technol, MatDept Dyestuff Technol, Inst Chem Technol, Dept Dyestuff Technol, NP Marg, Mumbai 400019, Maharashtra, India
关键词
Amides; Metal-free approach; Green chemistry; Heterogeneous catalysis; Recyclability; Solvent-free reaction condition; ONE-POT SYNTHESIS; EFFICIENT CATALYST; DIRECT AMIDATION; GRAPHITE OXIDE; TRANSAMIDATION; CARBOXAMIDES; CONVENIENT; OXIDATION;
D O I
10.1002/slct.202000870
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Herein, a highly efficient, metal-free, carbocatalyst, graphene oxide (GO) has been screened for the direct amidation of carboxylic acids with amines. The present catalytic system accessed a broad range of substrates to afford amides in excellent yields. A plausible reaction mechanism involving H-bonding with the reactants is described. Furthermore, the GO can be recycled and reused up to five cycles without substantial loss in catalytic activity.
引用
收藏
页码:8295 / 8300
页数:6
相关论文
共 38 条
[1]   Regio- and Enantioselective Friedel-Crafts Reactions of Indoles to Epoxides Catalyzed by Graphene Oxide: A Green Approach [J].
Acocella, Maria Rosaria ;
Mauro, Marco ;
Guerra, Gaetano .
CHEMSUSCHEM, 2014, 7 (12) :3279-3283
[2]   Direct amide formation from unactivated carboxylic acids and amines [J].
Allen, C. Liana ;
Chhatwal, A. Rosie ;
Williams, Jonathan M. J. .
CHEMICAL COMMUNICATIONS, 2012, 48 (05) :666-668
[3]   Transamidation of Carboxamides Catalyzed by Fe(III) and Water [J].
Becerra-Figueroa, Liliana ;
Ojeda-Porras, Andrea ;
Gamba-Sanchez, Diego .
JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (10) :4544-4552
[4]   The Uncatalyzed Direct Amide Formation Reaction - Mechanism Studies and the Key Role of Carboxylic Acid H-Bonding [J].
Charville, Hayley ;
Jackson, David A. ;
Hodges, George ;
Whiting, Andrew ;
Wilson, Mark R. .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2011, 2011 (30) :5981-5990
[5]   Synthesis of "Clean" and Well-Dispersive Pd Nanoparticles with Excellent Electrocatalytic Property on Graphene Oxide [J].
Chen, Xiaomei ;
Wu, Genghuang ;
Chen, Jinmei ;
Chen, Xi ;
Xie, Zhaoxiong ;
Wang, Xiaoru .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (11) :3693-3695
[6]   Nonclassical Routes for Amide Bond Formation [J].
de Figueiredo, Renata Marcia ;
Suppo, Jean-Simon ;
Campagne, Jean-Marc .
CHEMICAL REVIEWS, 2016, 116 (19) :12029-12122
[7]  
Dreyer D.R., 2010, Angewandte Chemie International Edition, V49, P6813
[8]   Graphene Oxide: A Convenient Carbocatalyst for Facilitating Oxidation and Hydration Reactions [J].
Dreyer, Daniel R. ;
Jia, Hong-Peng ;
Bielawski, Christopher W. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (38) :6813-6816
[9]   Graphene oxide as a facile solid acid catalyst for the production of bioadditives from glycerol esterification [J].
Gao, Xiaoqing ;
Zhu, Shanhui ;
Li, Yongwang .
CATALYSIS COMMUNICATIONS, 2015, 62 :48-51
[10]   Graphene Oxide Promoted Oxidative Bromination of Anilines and Phenols in Water [J].
Ghorpade, Prashant Vasantrao ;
Pethsangave, Dattatray Appasha ;
Some, Surajit ;
Shankarling, Ganapati Subray .
JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (14) :7388-7397