A sustainable metal and base-free direct amidation of esters using water as a green solvent

被引：1

作者：

Rajendran, Nanthini ^{[1
]}

Kamaraj, Kiruthigadevi ^{[1
]}

Janakiraman, Saranya ^{[1
]}

Saral, Mary ^{[1
]}

Dixneuf, Pierre H. ^{[2
]}

Bheeter, Charles Beromeo ^{[1
]}

机构：

[1] Vellore Inst Technol, Sch Adv Sci, Dept Chem, Vellore 632014, Tamil Nadu, India

[2] Univ Rennes, ISCR, UMR CNRS 6226, F-35000 Rennes, France

来源：

RSC ADVANCES | 2023年 / 13卷 / 22期

关键词：

CATALYZED DIRECT AMIDATION; AMIDE BOND FORMATION; MILD; TRANSAMIDATION; PRECATALYST; CONVERSION; REAGENTS; LACTONES; CLEAVAGE;

D O I：

10.1039/d3ra02637j

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Herein, we report a simple and efficient synthetic approach for direct amidation of esters via C(acyl)-O bond cleavage without any additional reagents or catalysts, using only water as a green solvent. Subsequently, the reaction byproduct is recovered and utilized for the next phase of ester synthesis. This method emphasized metal-free, additive-free, and base-free characteristics making it a new, sustainable, and eco-friendly way to realize direct amide bond formation. In addition, the synthesis of the drug molecule diethyltoluamide and the Gram-scale synthesis of a representative amide are demonstrated.

引用

页码：14958 / 14962

页数：5

共 57 条

[1] Choosing the Right Coupling Reagent for Peptides: A Twenty-Five-Year Journey [J].

Albericio, Fernando ;

El-Faham, Ayman .

ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2018, 22 (07) :760-772

[2] Metal-catalysed approaches to amide bond formation [J].

Allen, C. Liana ;

Williams, Jonathan M. J. .

CHEMICAL SOCIETY REVIEWS, 2011, 40 (07) :3405-3415

[3] Decarbonylative C-H Coupling of Azoles and Aryl Esters: Unprecedented Nickel Catalysis and Application to the Synthesis of Muscoride A [J].

Amaike, Kazuma ;

Muto, Kei ;

Yamaguchi, Junichiro ;

Itami, Kenichiro .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (33) :13573-13576

[4]

Anderson N. G., 2012, PRACTICAL PROCESS RE, P89, DOI DOI 10.1016/B978-0-12-386537-3.00004-6

[5] Nickel-Catalyzed Amide Bond Formation from Methyl Esters [J].

Ben Halima, Taoufik ;

Masson-Makdissi, Jeanne ;

Newman, Stephen G. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (39) :12925-12929

[6] A Cross-Coupling Approach to Amide Bond Formation from Esters [J].

Ben Halima, Taoufik ;

Vandavasi, Jaya Kishore ;

Shkoor, Mohanad ;

Newman, Stephen G. .

ACS CATALYSIS, 2017, 7 (03) :2176-2180

[7] Activation of C-O and C-N Bonds Using Non-Precious-Metal Catalysis [J].

Boit, Timothy B. ;

Bulger, Ana S. ;

Dander, Jacob E. ;

Garg, Neil K. .

ACS CATALYSIS, 2020, 10 (20) :12109-12126

[8] Analysis of Past and Present Synthetic Methodologies on Medicinal Chemistry: Where Have All the New Reactions Gone? [J].

Brow, Dean G. ;

Bostrom, Jonas .

JOURNAL OF MEDICINAL CHEMISTRY, 2016, 59 (10) :4443-4458

[9] Catalytic amidation of unactivated ester derivatives mediated by trifluoroethanol [J].

Caldwell, Nicola ;

Jamieson, Craig ;

Simpson, Iain ;

Watson, Allan J. B. .

CHEMICAL COMMUNICATIONS, 2015, 51 (46) :9495-9498

[10] Ligand-Controlled Chemoselective C(acyl)-O Bond vs Caryl)-C Bond Activation of Aromatic Esters in Nickel Catalyzed C(sp2)-C(sp3) Cross-Couplings [J].

Chatupheeraphat, Adisak ;

Liao, Hsuan-Hung ;

Srimontree, Watchara ;

Guo, Lin ;

Minenkov, Yury ;

Poater, Albert ;

Cavallo, Luigi ;

Rueping, Magnus .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2018, 140 (10) :3724-3735

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