Continuous-flow dehydrative amidation between carboxylic acids and amines using modified mixed metal oxides as solid acid catalysts

Ishitani, Haruro; Takeno, Kota; Sasaya, Masahiro; Kobayashi, Shū

doi:10.1039/d3cy00937h

Catal. Sci. Technol.

2023

DOI: 10.1039/d3cy00937h

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Continuous-flow dehydrative amidation between carboxylic acids and amines using modified mixed metal oxides as solid acid catalysts

Haruro Ishitani,

Kota Takeno,

Masahiro Sasaya

et al.

Abstract: High performance molybdenum (vi)-supported Zr–Sn mixed oxides were applied in continuous-flow dehydrative amidation between aliphatic carboxylic acids and amines. The desired amides were obtained in high yields with sufficient space–time-yields.

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Direct Solvent‐Free Amide Bond Formation Catalyzed by Anatase‐TiO₂ Surface: Insight from Modeling

Fois,

Tabacchi

2024

Small Structures

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Amide bond formation processes are of paramount relevance for a broad spectrum of applications. Conventional amidation protocols typically rely on drastic reaction conditions and the use/disposal of large amounts of chemicals. These limitations may be bypassed by heterogeneously catalyzed amidation at dry conditions. However, progress is hindered because the mechanisms of these processes are largely unexplored. By using ab initio metadynamics, a concerted one‐step mechanism is proposed for the solvent‐free condensation of methylamine and formic acid on TiO2(101)‐anatase, leading to methylformamide with concomitant release of molecular water. The activation barrier—14.3 kcal mol−1—is in line with the mild conditions experimentally adopted in amide bond syntheses on TiO2 nanoparticles. The mechanism disclosed herein reveals the key role of Ti4+ sites located on stoichiometric (101) anatase surfaces in promoting amide‐bond formation at the TiO2/vapor interface. The acid strength of the adsorbed HCOOH molecules may be tuned by the HCOOH surface coverage, thus influencing the outcome of the amidation reaction. These molecular‐level insights may foster further endeavors to improve/upscale TiO2‐catalyzed amide syntheses at dry conditions, while raising the interest toward amidation processes at the surface/vapor interface promoted by economically and environmentally sustainable metal oxide nanomaterials.

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Direct Solvent‐Free Amide Bond Formation Catalyzed by Anatase‐TiO₂ Surface: Insight from Modeling

Fois,

Tabacchi

2024

Small Structures

View full text Add to dashboard Cite

show abstract

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Continuous-flow dehydrative amidation between carboxylic acids and amines using modified mixed metal oxides as solid acid catalysts

Abstract: High performance molybdenum (vi)-supported Zr–Sn mixed oxides were applied in continuous-flow dehydrative amidation between aliphatic carboxylic acids and amines. The desired amides were obtained in high yields with sufficient space–time-yields.

Cited by 1 publication

References 60 publications

Direct Solvent‐Free Amide Bond Formation Catalyzed by Anatase‐TiO₂ Surface: Insight from Modeling

Direct Solvent‐Free Amide Bond Formation Catalyzed by Anatase‐TiO₂ Surface: Insight from Modeling

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Continuous-flow dehydrative amidation between carboxylic acids and amines using modified mixed metal oxides as solid acid catalysts

Abstract: High performance molybdenum (vi)-supported Zr–Sn mixed oxides were applied in continuous-flow dehydrative amidation between aliphatic carboxylic acids and amines. The desired amides were obtained in high yields with sufficient space–time-yields.

Cited by 1 publication

References 60 publications

Direct Solvent‐Free Amide Bond Formation Catalyzed by Anatase‐TiO2 Surface: Insight from Modeling

Direct Solvent‐Free Amide Bond Formation Catalyzed by Anatase‐TiO2 Surface: Insight from Modeling

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Product

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About

Direct Solvent‐Free Amide Bond Formation Catalyzed by Anatase‐TiO₂ Surface: Insight from Modeling

Direct Solvent‐Free Amide Bond Formation Catalyzed by Anatase‐TiO₂ Surface: Insight from Modeling