Metal-Free Sustainable Synthesis of Amides via Oxidative Amidation Using Graphene Oxide as Carbocatalyst in Aqueous Medium

被引：9

作者：

Dandia, Anshu ^{[1
]}

Parihar, Sonam ^{[1
]}

Saini, Pratibha ^{[1
]}

Rathore, Kuldeep S. ^{[2
]}

Parewa, Vijay ^{[1
]}

机构：

[1] Univ Rajasthan, Dept Chem, Ctr Adv Studies, Jaipur 302004, Rajasthan, India

[2] Arya Coll Engn & IT, Dept Phys, Jaipur, Rajasthan, India

来源：

CATALYSIS LETTERS | 2019年 / 149卷 / 11期

关键词：

Carbocatalyst; Oxidative amidation; Metal-free synthesis; BENZYL ALCOHOLS; ALDEHYDES; NANOPARTICLES; AMINES; GO; REARRANGEMENT; ESTERS;

D O I：

10.1007/s10562-019-02878-5

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

We describe an efficient, clean and metal-free procedure for the synthesis of amides via oxidative amidation of aldehydes with anilines using graphene oxide (GO) as a recyclable catalyst and KBrO3 as a mild oxidant in aqueous medium under microwave irradiation. GO nanosheets were prepared and characterized by XRD, TEM, SEM, and FT-IR, analyses. GO showed high compatibility with KBrO3 in water and offered high TOF value (1.30 x 10(-3) mol g(-1) min(-1)). GO oxygen functionalities catalyze the oxidative amidation effectively in mild condition with high recyclability. A plausible mechanism was proposed by the isolating the intermediate.

引用

页码：3169 / 3175

页数：7

共 42 条

[1] Direct Transamidation Reactions: Mechanism and Recent Advances
Acosta-Guzman, Paola
Mateus-Gomez, Alejandra
Gamba-Sanchez, Diego
[J]. MOLECULES, 2018, 23 (09):
[2] Oxaziridine rearrangements in asymmetric synthesis
Aube, J
[J]. CHEMICAL SOCIETY REVIEWS, 1997, 26 (04) : 269 - 277
[3] Graphene oxide (GO) catalyzed transamidation of aliphatic amides: An efficient metal-free procedure
Bhattacharya, Suchandra
Ghosh, Pranab
Basu, Basudeb
[J]. TETRAHEDRON LETTERS, 2018, 59 (10) : 899 - 903
[4] Sulfonated graphene oxide-catalyzed N-acetylation of amines with acetonitrile under sonication
Brahmayya, Manuri
Suen, Shing-Yi
Dai, Shenghong A.
[J]. JOURNAL OF THE TAIWAN INSTITUTE OF CHEMICAL ENGINEERS, 2018, 83 : 174 - 183
[5] Chemat F, 1998, J MICROWAVE POWER EE, V33, P88
[6] Graphene Oxide, Highly Reduced Graphene Oxide, and Graphene: Versatile Building Blocks for Carbon-Based Materials
Compton, Owen C.
Nguyen, SonBinh T.
[J]. SMALL, 2010, 6 (06) : 711 - 723
[7] Cupido T, 2007, CURR OPIN DRUG DISC, V10, P768
[8] Ag NPs decked GO composite as a competent and reusable catalyst for 'ON WATER' chemoselective synthesis of pyrano[2,3-c:6,5-c′]dipyrazol]-2-ones
Dandia, Anshu
Gupta, Shyam L.
Indora, Aayushi
Saini, Pratibha
Parewa, Vijay
Rathore, Kuldeep S.
[J]. TETRAHEDRON LETTERS, 2017, 58 (12) : 1170 - 1175
[9] Imposed hydrophobic interactions by NaCl: accountable attribute for the synthesis of spiro-[acenaphthylene-1,5′-pyrrolo[1,2-c]thiazole] derivatives via 1,3-dipolar cycloaddition reaction in aqueous medium
Dandia, Anshu
Parewa, Vijay
Kumari, Sukhbeer
Bansal, Sarika
Sharma, Amit
[J]. GREEN CHEMISTRY, 2016, 18 (08) : 2488 - 2499
[10] Amidic C-N bond cleavage of isatin: chemoselective synthesis of pyrrolo[2,3,4-kl] acridin-1-ones using Ag NPs decorated rGO composite as an efficient and recoverable catalyst under microwave irradiation
Dandia, Anshu
Sharma, Amit
Parewa, Vijay
Kumawat, Begraj
Rathore, Kuldeep S.
Sharma, Amit
[J]. RSC ADVANCES, 2015, 5 (111): : 91888 - 91902

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