Facile Amide Bond Formation from Carboxylic Acids and Isocyanates

Sasaki, Kaname; Crich, David

doi:10.1021/ol200531k

Cited by 103 publications

(52 citation statements)

References 27 publications

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“…Based on the IR results, the probable structure of PSS-PPDI with a sulfonamide derivative was obtained as a product of the reaction between the isocyanate functions and a sulfonic acid group (Fig. 2), which is matched analogically with the reaction between a carboxylic acid group and an isocyanate function leading to an unstable carbamic anhydride which decomposes to an amide and carbon dioxide (Hawkins et al, 1997;Sugama et al, 1988;Nabuurs et al, 1999;Melchiors et al, 2000;Sasaki & Crich, 2011).…”

Section: Atr-ftir Analysismentioning

confidence: 99%

Preparation, characterization and ion adsorption properties of functionalized polystyrene modified with 1,4-phenylene diisocyanate and diethylenetriamine

2015

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In the present work, linear polystyrene (PS) was functionalized by a sulfonation reaction providing sulfonated polystyrene (PSS). Then, the PSS polymer chains were cross-linked with the 1,4-phenylene diisocyanate (PPDI) group in tetrahydrofuran (THF), which led to a PSS-PPDI polymer. The PSS-PPDI was grafted by diethylenetriamine (DETA) in a solution of THF to obtain polymer PSS-PPDI-DETA. Their structures were characterized by infrared spectroscopy (ATR-FTIR), elemental analysis (EA), differential scanning calorimetry (DSC), thermogravemetric (TGA), thermodynamic (DTA) and differential thermogravimetric (DTG) analysis. Subsequently, the obtained polymers were tested for their ability to remove some metal ions from aqueous media such as Zn 2+ , Cd 2+ and Co 2+ .

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Section: Atr-ftir Analysismentioning

confidence: 99%

Preparation, characterization and ion adsorption properties of functionalized polystyrene modified with 1,4-phenylene diisocyanate and diethylenetriamine

2015

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“…Still, some disadvantages such as low product yields, longer reaction time, high reactant amount, lack of catalyst recyclability, contamination of the product due to catalyst leaching, and the formation of undesirable products in stoichiometric amounts are associated with these methods. As a result, the heterogeneous catalysts which are highly efficient, ecologically correct, recyclable, and environment‐friendly are most demanding for advanced catalytic methods for the solvent‐free aminolysis of triglycerides . Biochar‐based (catalyst 6 wt%, yield 98%, reaction time 2.5 hours), zirconia‐alumina nanocatalyst (catalyst 3 wt%, yield 91.6%, reaction time 4 hours), spongy Ni/Fe carbonate‐fluorapatite (catalyst 9.5 wt%, yield 96%, reaction time 2 hours), sodium‐doped nanohydroxyapatite (catalyst 6 wt%, yield 98%, reaction time 2.5 hours), porous BaSnO 3 (catalyst 6 wt%, 96% yield, reaction time 2 hours), CaO/MCM‐41 nanocatalyst (catalyst 5 wt%, yield 96.8%, reaction time 6 hours), and alkali metal‐doped CaO‐based heterogeneous catalysts were reported for natural triglycerides conversion to fatty acid alkyl derivatives.…”

Section: Introductionmentioning

confidence: 99%

One‐pot solvent‐free transformation of natural triglycerides to ester and amide derivatives over CaO@KC nanostructured catalysts

2020

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Summary In the present report, the fatty acid alkyl esters and fatty acid amides were synthesized from natural triglycerides by highly selective solvent‐free one‐step methods using 3.5‐CaO@KC‐400 nanocrystals as a heterogeneous catalyst. A modified wetness chemical impregnation method was used to prepared potassium carbonate‐doped CaO, ZnO, and MgO nanocrystals. The prepared 3.5‐CaO@KC‐400 nanocrystals were found as the most efficient heterogeneous catalyst (5%, w/w) for amidation (6:1 M ratio of diethanolamine/oil, 110°C) and transesterification (12:1 M ratio of methanol/oil, 65°C) of waste cooking oil and took 30 minutes for the completion of both the reactions. The 3.5‐CaO@KC‐400 nanocrystals were found to be efficient at room temperature also and reused for 10 reaction cycles for both reactions. The pseudo‐first‐order kinetic model was applied and the first‐order rate constant was calculated as 0.15 minute−1 and 0.103 minute−1 for the amidation and transesterification reactions of waste cooking oil, respectively.

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“…For example, a widely used method is condensation of an amine with an activated carboxylic acid functionality 3a–e. More recently, coupling reactions that involve thioacids as alternatives to the carboxylic acid functionality,4 and azides,5a–d sulfonamides,6a–c isocyanates,7a–c and isonitriles8 as alternatives to the amine nitrogen functionality have been developed. Amide formation by direct addition of Grignard reagent to isocyanate has also been reported 9.…”

Section: Introductionmentioning

confidence: 99%

Acid‐Promoted Chemoselective Introduction of Amide Functionality onto Aromatic Compounds Mediated by an Isocyanate Cation Generated from Carbamate

Sumita

Kurouchi

Otani

et al. 2014

Chemistry An Asian Journal

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Carbamates have been used as precursors of isocyanates, but heating in the presence of strong acids is required because cleavage of the C-O bond in carbamates is energy-demanding even in acid media. Direct amidation of aromatic compounds by isocyanate cations generated at room temperature from carbamoyl salicylates in trifluoromethanesulfonic acid (TfOH) was examined. Carbamates with ortho-salicylate as an ether group (carbamoyl salicylates) showed dramatically accelerated O-C bond dissociation in TfOH, which resulted in facile generation of the isocyanate cation. These chemoselective intermolecular aromatic amidation reactions proceeded even at room temperature and showed good compatibility with other electrophilic functionalities and high discrimination between N-monosubstituted carbamate and N,N-disubstituted carbamate. The reaction rates of secondary and tertiary amide formation were markedly different, and this difference was utilized to achieve successive (tandem) amidation reactions of molecules with an N-monosubstituted carbamate and an N,N-disubstituted carbamate with two kinds of aromatic compounds.

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Facile Amide Bond Formation from Carboxylic Acids and Isocyanates

Cited by 103 publications

References 27 publications

Preparation, characterization and ion adsorption properties of functionalized polystyrene modified with 1,4-phenylene diisocyanate and diethylenetriamine

Preparation, characterization and ion adsorption properties of functionalized polystyrene modified with 1,4-phenylene diisocyanate and diethylenetriamine

One‐pot solvent‐free transformation of natural triglycerides to ester and amide derivatives over CaO@KC nanostructured catalysts

Acid‐Promoted Chemoselective Introduction of Amide Functionality onto Aromatic Compounds Mediated by an Isocyanate Cation Generated from Carbamate

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