ChemInform Abstract: Metal-Catalyzed Approaches to Amide Bond Formation

A new phosphonium based coupling reagent DEPO-B has been synthesized from 5- (hydroxyimino)-1,3-dimethylpyrimidine-2,4,6 (1H,3H,5H)-trione (Oxyma B) and diethyl chlorophosphate in presence of base. It is a solid material and the hydrolytic stability and solubility was evaluated for confirming its capability for usage in automated peptide synthesizer.

Download Full-text

A Review of Amide Bond Formation in Microwave Organic Synthesis

Current Organic Synthesis ◽

10.2174/1570179411666140321180857 ◽

2014 ◽

Vol 11 (4) ◽

pp. 592-604 ◽

Cited By ~ 18

Author(s):

Natalia Lukasik ◽

Ewa Wagner-Wysiecka

Keyword(s):

Organic Synthesis ◽

Bond Formation ◽

Amide Bond ◽

Amide Bond Formation

Download Full-text

A computational study on the mechanism of ynamide-mediated amide bond formation from carboxylic acids and amines

Organic & Biomolecular Chemistry ◽

10.1039/c7ob01378g ◽

2017 ◽

Vol 15 (30) ◽

pp. 6367-6374 ◽

Cited By ~ 12

Author(s):

Song-Lin Zhang ◽

Hai-Xing Wan ◽

Zhu-Qin Deng

Keyword(s):

Reaction Mechanism ◽

Carboxylic Acids ◽

Computational Study ◽

Bond Formation ◽

Amide Bond ◽

Reactivity Pattern ◽

Amide Bond Formation ◽

Coupling Reagent ◽

Catalytic Effects ◽

Acid Substrate

A detailed computational study is presented on the reaction mechanism of ynamide-mediated condensation of carboxylic acids with amines to produce amides, which elucidates the reactivity pattern of the coupling reagent ynamide and discloses crucial bifunctional catalytic effects of the carboxylic acid substrate during aminolysis.

Download Full-text

Ab initio study of catalyzed and uncatalyzed amide bond formation as a model for peptide bond formation: Ammonia-Glycine reactions

Journal of Computational Chemistry ◽

10.1002/jcc.540040402 ◽

1983 ◽

Vol 4 (4) ◽

pp. 449-460 ◽

Cited By ~ 9

Author(s):

Tetsuro Oie ◽

Gilda H. Loew ◽

Stanley K. Burt ◽

Robert D. Macelroy

Keyword(s):

Ab Initio ◽

Bond Formation ◽

Peptide Bond ◽

Amide Bond ◽

Ab Initio Study ◽

Peptide Bond Formation ◽

Amide Bond Formation

Download Full-text

Green Amide Bond Formation in Water via Direct Coupling of Metal Carboxylate Salts with Ammonium Salts at Room Temperature

Organic & Biomolecular Chemistry ◽

10.1039/d1ob02064a ◽

2021 ◽

Author(s):

Truong Thanh Tung ◽

John Nielsen

Keyword(s):

Room Temperature ◽

Bond Formation ◽

Direct Coupling ◽

Ammonium Salts ◽

Amide Bond ◽

Metal Carboxylate ◽

Amide Bond Formation ◽

Simple Protocol

Herein, we report the green, expedite, and practically simple protocol for direct coupling of carboxylate salts and ammonium salts under ACN/H2O conditions at room temperature without the addition of tertiary...

Download Full-text

Ruthenium-Based Catalytic Systems Incorporating a Labile Cyclooctadiene Ligand with N-Heterocyclic Carbene Precursors for the Atom-Economic Alcohol Amidation Using Amines

Molecules ◽

10.3390/molecules23102413 ◽

2018 ◽

Vol 23 (10) ◽

pp. 2413 ◽

Cited By ~ 7

Author(s):

Cheng Chen ◽

Yang Miao ◽

Kimmy De Winter ◽

Hua-Jing Wang ◽

Patrick Demeyere ◽

...

Keyword(s):

Catalytic System ◽

High Resolution Mass Spectrometry ◽

Amide Bond ◽

Catalyst Loading ◽

Catalytic Systems ◽

Amide Bond Formation ◽

Highly Active ◽

Metal Catalyzed ◽

Ru Species

Transition-metal-catalyzed amide-bond formation from alcohols and amines is an atom-economic and eco-friendly route. Herein, we identified a highly active in situ N-heterocyclic carbene (NHC)/ruthenium (Ru) catalytic system for this amide synthesis. Various substrates, including sterically hindered ones, could be directly transformed into the corresponding amides with the catalyst loading as low as 0.25 mol.%. In this system, we replaced the p-cymene ligand of the Ru source with a relatively labile cyclooctadiene (cod) ligand so as to more efficiently obtain the corresponding poly-carbene Ru species. Expectedly, the weaker cod ligand could be more easily substituted with multiple mono-NHC ligands. Further high-resolution mass spectrometry (HRMS) analyses revealed that two tetra-carbene complexes were probably generated from the in situ catalytic system.

Download Full-text