From A<sup>3</sup>/KA<sup>2</sup>to AYA/KYA multicomponent coupling reactions with terminal ynamides as alkyne surrogates – a direct, green route to γ-amino-ynamides

Schlimpen, Fabian; AST, Tun; Benneteau, Valerie; Pale, Patrick; Chassaing, Stefan

doi:10.1039/d2gc00966h

Cited by 3 publications

(1 citation statement)

References 58 publications

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“…The SSIE method discussed in this study have also been used to synthesise Cu I -exchanged FAU zeolites that have been investigated as a catalyst for C-C bond Glaser-type homocoupling reactions by Kuhn et al [21]. Furthermore, the Cu I -FAU zeolite has been shown to be applicable as a catalyst in several other types of organic synthesis [22][23][24][25][26]. This truly shows the adversity of Cu-sites in zeolites.…”

Section: Introductionmentioning

confidence: 76%

Copper-zeolites Prepared by Solid-state Ion Exchange - Characterization and Evaluation for the Direct Conversion of Methane to Methanol

et al. 2022

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Direct conversion of methane to methanol (MTM) over Cu-zeolites is a so-called “dream reaction” for the chemical industry. There is still a lot that can be done in order to optimize the reaction by e.g. achieving a deeper understanding of the reaction mechanism and the nature of the Cu-sites. In this study, we investigated a solid-state ion exchange method to incorporate CuI ions into zeolites (MOR, BEA, ZSM-5 and FAU), as a more scalable technique. The solid-state ion exchange led to a Cu/Al ration of about 0.8, however with a heterogeneous distribution of Cu. Regardless, Fourier transform-infrared spectroscopy still revealed that most Brønsted acid sites were exchanged in all four samples. Further, CH4-temperature programmed reaction experiments showed that some Cu-sites formed were reactive towards CH4, with CuI-MOR and CuI-FAU having the largest CH4 consumption. Ultimately, the CuI-zeolites were tested in the MTM reaction and proved capable of producing methanol, even without the presence of Brønsted sites. A MOR with lower Cu/Al ratio (0.30) was also tested for comparison, and as this sample obtained a much higher productivity than the CuI-MOR with high Cu-loading (0.10 vs. 0.03 molMeOH/molCu), it was demonstrated that some fine-tuning is necessary to obtain the active Cu sites for methane activation.

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Section: Introductionmentioning

confidence: 76%

Copper-zeolites Prepared by Solid-state Ion Exchange - Characterization and Evaluation for the Direct Conversion of Methane to Methanol

et al. 2022

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Catalytic C–C Bond Forming Reaction to Imines

Kokić,

Andrijević,

Opsenica

2024

Reference Module in Chemistry, Molecular Sciences and Chemical Engineering

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Peptide Diversification through Addition Reaction of Free Carboxylic Acids to Ynamides

2023

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Peptide modification has emerged as an important topic in the academic community and pharmaceutical industry. However, they are primarily focused on the diversification of amines, thiols, and alcohols. Direct and chemoselective modification of acid residues in peptides is relatively underdeveloped. In this context, we report a novel and efficient method for the direct functionalization of acid residues in peptides. By using ynamides as reaction partners, the adducts are rapidly obtained in moderate to excellent yields at room temperature in water. This approach shows excellent chemoselectivity and a broad scope including dipeptides bearing unprotected Trp or Tyr residue and free Ser or Gln residue.

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From A³/KA²to AYA/KYA multicomponent coupling reactions with terminal ynamides as alkyne surrogates – a direct, green route to γ-amino-ynamides

Abstract: The copper-zeolite catalysed three-component coupling reaction between an aldehyde or a ketone, a terminal ynamide and an amine is reported. The method, dubbed AYA (i.e. Aldehyde-Ynamide-Amine) and KYA (i.e. Ketone-Ynamide-Amine),...

Cited by 3 publications

References 58 publications

Copper-zeolites Prepared by Solid-state Ion Exchange - Characterization and Evaluation for the Direct Conversion of Methane to Methanol

Copper-zeolites Prepared by Solid-state Ion Exchange - Characterization and Evaluation for the Direct Conversion of Methane to Methanol

Catalytic C–C Bond Forming Reaction to Imines

Peptide Diversification through Addition Reaction of Free Carboxylic Acids to Ynamides

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From A3/KA2to AYA/KYA multicomponent coupling reactions with terminal ynamides as alkyne surrogates – a direct, green route to γ-amino-ynamides

Abstract: The copper-zeolite catalysed three-component coupling reaction between an aldehyde or a ketone, a terminal ynamide and an amine is reported. The method, dubbed AYA (i.e. Aldehyde-Ynamide-Amine) and KYA (i.e. Ketone-Ynamide-Amine),...

Cited by 3 publications

References 58 publications

Copper-zeolites Prepared by Solid-state Ion Exchange - Characterization and Evaluation for the Direct Conversion of Methane to Methanol

Copper-zeolites Prepared by Solid-state Ion Exchange - Characterization and Evaluation for the Direct Conversion of Methane to Methanol

Catalytic C–C Bond Forming Reaction to Imines

Peptide Diversification through Addition Reaction of Free Carboxylic Acids to Ynamides

Contact Info

Product

Resources

About

From A³/KA²to AYA/KYA multicomponent coupling reactions with terminal ynamides as alkyne surrogates – a direct, green route to γ-amino-ynamides