Matches in SemOpenAlex for { <https://semopenalex.org/work/W4250871910> ?p ?o ?g. }
Showing items 1 to 59 of
59
with 100 items per page.
- W4250871910 abstract "<p>Solid-state reactions using mechanochemical activation have emerged as solvent-free atom-efficient strategies for sustainable chemistry. Herein we report a new mechanochemical approach for the amide coupling of carboxylic acids and amines, mediated by combination of (1-сyano-2-ethoxy-2-oxoethylidenaminooxy)dimethylaminomorpholinocarbenium hexafluorophosphate (COMU) or <i>N</i>,<i>N</i>,<i>N</i>′,<i>N</i>′-tetramethylchloroformamidinium hexafluorophosphate (TCFH) and K<sub>2</sub>HPO<sub>4</sub>. The method delivers a range of amides in high 70–96% yields and fast reaction rates. The reaction protocol is mild, maintains the integrity of the adjacent to carbonyl stereocenters, and streamlines isolation procedure for solid amide products. Minimal waste is generated due to the absence of bulk solvent. We show that K<sub>2</sub>HPO<sub>4</sub> plays a dual role, acting as a base and a precursor of reactive acyl phosphate species. Amide bonds from hindered carboxylic acids and low-nucleophilic amines can be assembled within 90 min by using TCFH in combination with K<sub>2</sub>HPO<sub>4</sub> or <i>N</i>-methylimidazole. The developed mechanochemical liquid-assisted amidation protocols were successfully applied to the challenging couplings of all six carboxylate functions of biotin[6]uril macrocycle with phenylalanine methyl ester, resulting in an 80% yield of highly pure hexa-amide-biotin[6]uril. In addition, fast and high-yielding synthesis of peptides and versatile amide compounds can be performed in a safe and environmentally benign manner, as verified by green metrics.<b></b></p>" @default.
- W4250871910 created "2022-05-12" @default.
- W4250871910 creator A5000760785 @default.
- W4250871910 creator A5024350856 @default.
- W4250871910 creator A5026325664 @default.
- W4250871910 creator A5050375654 @default.
- W4250871910 creator A5068512438 @default.
- W4250871910 creator A5087668997 @default.
- W4250871910 date "2020-07-30" @default.
- W4250871910 modified "2023-09-23" @default.
- W4250871910 title "Rapid Mechanochemical Synthesis of Amides with Uronium-Based Coupling Reagents, a Method for Hexa-amidation of Biotin[6]uril" @default.
- W4250871910 doi "https://doi.org/10.26434/chemrxiv.12735377.v1" @default.
- W4250871910 hasPublicationYear "2020" @default.
- W4250871910 type Work @default.
- W4250871910 citedByCount "0" @default.
- W4250871910 crossrefType "posted-content" @default.
- W4250871910 hasAuthorship W4250871910A5000760785 @default.
- W4250871910 hasAuthorship W4250871910A5024350856 @default.
- W4250871910 hasAuthorship W4250871910A5026325664 @default.
- W4250871910 hasAuthorship W4250871910A5050375654 @default.
- W4250871910 hasAuthorship W4250871910A5068512438 @default.
- W4250871910 hasAuthorship W4250871910A5087668997 @default.
- W4250871910 hasBestOaLocation W42508719101 @default.
- W4250871910 hasConcept C154881586 @default.
- W4250871910 hasConcept C155647269 @default.
- W4250871910 hasConcept C161790260 @default.
- W4250871910 hasConcept C178790620 @default.
- W4250871910 hasConcept C185592680 @default.
- W4250871910 hasConcept C2777598222 @default.
- W4250871910 hasConcept C2778074193 @default.
- W4250871910 hasConcept C2778439535 @default.
- W4250871910 hasConcept C40875361 @default.
- W4250871910 hasConcept C71240020 @default.
- W4250871910 hasConceptScore W4250871910C154881586 @default.
- W4250871910 hasConceptScore W4250871910C155647269 @default.
- W4250871910 hasConceptScore W4250871910C161790260 @default.
- W4250871910 hasConceptScore W4250871910C178790620 @default.
- W4250871910 hasConceptScore W4250871910C185592680 @default.
- W4250871910 hasConceptScore W4250871910C2777598222 @default.
- W4250871910 hasConceptScore W4250871910C2778074193 @default.
- W4250871910 hasConceptScore W4250871910C2778439535 @default.
- W4250871910 hasConceptScore W4250871910C40875361 @default.
- W4250871910 hasConceptScore W4250871910C71240020 @default.
- W4250871910 hasLocation W42508719101 @default.
- W4250871910 hasOpenAccess W4250871910 @default.
- W4250871910 hasPrimaryLocation W42508719101 @default.
- W4250871910 hasRelatedWork W10162337 @default.
- W4250871910 hasRelatedWork W11683439 @default.
- W4250871910 hasRelatedWork W12117845 @default.
- W4250871910 hasRelatedWork W14798055 @default.
- W4250871910 hasRelatedWork W24342510 @default.
- W4250871910 hasRelatedWork W27493539 @default.
- W4250871910 hasRelatedWork W6644995 @default.
- W4250871910 hasRelatedWork W7165967 @default.
- W4250871910 hasRelatedWork W7212558 @default.
- W4250871910 hasRelatedWork W7423718 @default.
- W4250871910 isParatext "false" @default.
- W4250871910 isRetracted "false" @default.
- W4250871910 workType "article" @default.