A comparative study of amide-bond forming reagents in aqueous media – Substrate scope and reagent compatibility

Badland, Matthew; Crook, Robert; Delayre, Bastien; Fussell, Steven J.; Gladwell, Iain R.; Hawksworth, Michael; Howard, Roger M.; Walton, Robert; Weisenburger, Gerald A.

doi:10.1016/j.tetlet.2017.10.014

Cited by 31 publications

(24 citation statements)

References 26 publications

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“…Because it is difficult to directly induce the formation of amide functional groups on the carbon surface, the carbon surface was firstly activated by means of strong acids including a combination of H 2 SO 4 and HNO 3 in order to introduce COOH functional groups on the carbon surface, and the resulting COOH functional groups were converted into amide functional groups by means of a coupling reaction using N , N ‐diisopropylcarbodiimide (DIC), 2‐hydroxypyridine 1‐oxide (HOPO), and NH 3 . Here, we note that direct conversion of functional group from COOH to amide is thermodynamically forbidden; thus, it is required to employ such a coupling reagent to create amide functional groups on the carbon surface . After the first chemical reaction (COOH functionalization) was completed, the surface state was observed by mean s of an SEM, as shown in Figures a and 2b.…”

Section: Resultsmentioning

confidence: 99%

Amide‐Functionalized Porous Carbonaceous Anode Materials for Lithium‐Ion Batteries

et al. 2019

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Porous carbonaceous anode materials have received considerable attention as an alternative anode material, however, there is a critical bottleneck as it suffers from a large irreversible specific capacity loss over several initial cycles owing to undesired surface reactions. In order to suppress undesired surface reactions of porous carbonaceous anode material, here, we suggest a simple and convenient two‐step surface modification approach that allows the embedding of an amide functional group on the surface of a porous carbonaceous anode, which effectively improves the surface stability. In this approach, the porous carbonaceous anode material is firstly activated by means of strong acid treatment comprising a combination of H2SO4 and HNO3, and it is subjected to further modification by means of an amide coupling reaction. Our additional systematic analyses confirm that the acid functional group effectively transforms into the amide functional group. The resulting amide‐functionalized porous carbon exhibits an improved electrochemical performance: the initial discharge specific capacity is greatly reduced to less than 2,620 mA h g−1 and charge specific capacity is well still remained, indicating stabling cycling performance of the cell.

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Section: Resultsmentioning

confidence: 99%

Amide‐Functionalized Porous Carbonaceous Anode Materials for Lithium‐Ion Batteries

et al. 2019

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“…Badland et al have reported an extensive study on the identication of aqueous coupling conditions for the solution-phase synthesis of amides. 97 Initially, a wide range of coupling reagents based on carbodiimide, triazine, quinoline, uronium/aminium, phosphonium and imidazolium chemistry were screened for the coupling reaction between benzoic acid and benzylamine. The best coupling agents from the preliminary screen were optimized for the same coupling reaction in a mixture of water and MeCN (1 : 1), followed by determination of the substrate scope and an evaluation of aqueous stability.…”

Section: Water-based Sppsmentioning

confidence: 99%

Greening the synthesis of peptide therapeutics: an industrial perspective

et al. 2020

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“…100 DMF alone features in 47% of such reactions examined as part of an interrogation of SciFinder content. 106b The exploitation of micellar conditions in water is one means of deliberately avoiding the use of these dipolar, aprotic solvents, 107 and their associated safety and regulatory liabilities (vide supra). Success with the synthesis of a number of pharmaceutically relevant molecules has been observed with the use of TPGS-750-M (3) (Scheme 14).…”

Section: Amidationmentioning

confidence: 99%

Micelle-Mediated Chemistry in Water for the Synthesis of Drug Candidates

Steven¹

2019

Synthesis

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Micellar reaction conditions, in a predominantly aqueous medium, have been developed for transformations commonly used by synthetic chemists working in the pharmaceutical industry to discover and develop drug candidates. The reactions covered in this review are the Suzuki–Miyaura, Miyaura borylation, Sonogashira coupling, transition-metal-catalysed CAr–N coupling, SNAr, amidation, and nitro reduction. Pharmaceutically relevant examples of these applications will be used to show how micellar conditions can offer advantages in yield, operational ease, amount of waste generated, transition-metal catalyst loading, and safety over the use of organic solvents, irrespective of the setting in which they are used.1 Introduction2 Micelles as Solubilising Agents3 Micelles as Nanoreactors4 Designer Surfactants5 A Critical Evaluation of the Case for Chemistry in Micelles6 Scope of Review7 Suzuki–Miyaura Coupling8 Miyaura Borylation9 Sonogashira Coupling10 Transition-Metal-Catalysed CAr–N Couplings11 SNAr12 Amidation13 Nitro Reduction14 Micellar Sequences15 Summary and Outlook

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A comparative study of amide-bond forming reagents in aqueous media – Substrate scope and reagent compatibility

Cited by 31 publications

References 26 publications

Amide‐Functionalized Porous Carbonaceous Anode Materials for Lithium‐Ion Batteries

Amide‐Functionalized Porous Carbonaceous Anode Materials for Lithium‐Ion Batteries

Greening the synthesis of peptide therapeutics: an industrial perspective

Micelle-Mediated Chemistry in Water for the Synthesis of Drug Candidates

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