N-Heterocyclic carbene supported zinc catalysed <i>N</i>-formylation of diverse N–H functionalities with carbon dioxide under ambient conditions

Rit, Arnab; Sahoo, Sangita; Manna, Subarna

doi:10.1039/d3cy00401e

Cited by 6 publications

(2 citation statements)

References 54 publications

(29 reference statements)

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“…For the past decade, various Lewis acid catalysts have been developed for the reductive carbon dioxide fixation to formamides. − ,− For example, homogeneous catalysts bearing Zn, Cu, and Fe have been reported with TONs of 30–198 and TOFs of 1–33 h –1 for the reductive carbon dioxide fixation with N -methyl- N -phenylamine to N -methyl- N -phenylformamide at temperatures of 25–60 °C (refer to Table S2 for recent homogeneous catalytic systems). − …”

Section: Resultsmentioning

confidence: 99%

“…Recently, the reductive carbon dioxide fixation to formamides has attracted significant attention from scientists due to its mild reaction conditions. − The reaction of carbon dioxide with amines in the presence of silanes can induce the formation of formamides. Efficient Lewis acid catalysts enable this conversion to take place even at room temperature. − …”

Section: Introductionmentioning

confidence: 99%

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Zinc Gallate Nanoplates on Microporous Organic Hollow Nanoplatforms for Enhanced Reductive CO₂ Fixation to Formamides

Kim,

Jang,

et al. 2024

ACS Appl. Nano Mater.

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This work suggests an engineering methodology for catalytic 2D materials to achieve more efficient catalytic systems. Zinc gallate (ZnG), a Lewis acidic material with a thin 2D morphology, can easily form aggregates through layer–layer packing. Inner parts of ZnG aggregates would have difficulty in interacting with substrates. By coating hollow microporous organic polymer (H-MOP) supports with ZnG, the catalytic performance of ZnG can be enhanced due to facilitated contact of substrates with Zn species in shells. H-MOP@ZnG-2 with an optimal ZnG coating showed a much enhanced catalytic performance for the reductive carbon dioxide fixation with amines to formamides compared with ZnG. Various amines can be utilized in the reductive carbon dioxide fixation to formamides. In addition, H-MOP@ZnG-2 showed recyclability, maintaining its catalytic performance for five successive reactions.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Zinc Gallate Nanoplates on Microporous Organic Hollow Nanoplatforms for Enhanced Reductive CO₂ Fixation to Formamides

Kim,

Jang,

et al. 2024

ACS Appl. Nano Mater.

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Highly Efficient Thiolate‐Based Ionic Liquid Catalysts for Reduction of CO₂: Selective N‐Functionalization of Amines to Form N‐Formamides and N‐Methylamines

Wu,

Niu,

Hou

et al. 2024

Chemistry A European J

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Developing efficient catalysts to convert CO2 into value‐added chemicals is valuable for reducing carbon emissions. Herein, a kind of novel thiolate‐based ionic liquid with sulfur as the active site was designed and synthesized, which served as highly efficient catalyst for the reductive functionalization of CO2 by amines and hydrosilane. By adjusting the CO2 pressure, various formamides and methylamines were selectively obtained in high yields. Remarkably, at the catalyst loading of 0.1 mol%, the N‐formylation reaction of N‐methylaniline exhibited an impressive turnover frequency (TOF) up to 600 h‐1. This IL catalyst displayed the highest activity compared to the reported non‐transition‐metal catalysts, which could be attributed to the multiple roles of the IL in activating hydrosilane, amine and CO2. In addition, control experiments and NMR monitoring experiments provided evidence that the reduction of CO2 by hydrosilane yielded formoxysilane intermediates that subsequently reacted with amines to form N‐formylated products. Alternatively, the formoxysilane intermediates could further react with hydrosilane and amine to produce 4‐electron‐reduced aminal products. These aminal products served as crucial intermediates in the N‐methylation reactions.

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One-pot two-step reduction of CO2 with amines and NaBH4 to N-substituted compounds at atmospheric pressure

Wang,

Wei

et al. 2024

Journal of CO2 Utilization

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N-Heterocyclic carbene supported zinc catalysed N-formylation of diverse N–H functionalities with carbon dioxide under ambient conditions

Abstract: Reductive functionalization of CO2 for the synthesis of valuable formamide derivatives remains a challenge. Herein, we report a heteroditopic NHC ligand-supported environment-friendly zinc catalysed effective N-formylation of N-H moieties with...

Cited by 6 publications

References 54 publications

Zinc Gallate Nanoplates on Microporous Organic Hollow Nanoplatforms for Enhanced Reductive CO₂ Fixation to Formamides

Zinc Gallate Nanoplates on Microporous Organic Hollow Nanoplatforms for Enhanced Reductive CO₂ Fixation to Formamides

Highly Efficient Thiolate‐Based Ionic Liquid Catalysts for Reduction of CO₂: Selective N‐Functionalization of Amines to Form N‐Formamides and N‐Methylamines

One-pot two-step reduction of CO2 with amines and NaBH4 to N-substituted compounds at atmospheric pressure

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N-Heterocyclic carbene supported zinc catalysed N-formylation of diverse N–H functionalities with carbon dioxide under ambient conditions

Abstract: Reductive functionalization of CO2 for the synthesis of valuable formamide derivatives remains a challenge. Herein, we report a heteroditopic NHC ligand-supported environment-friendly zinc catalysed effective N-formylation of N-H moieties with...

Cited by 6 publications

References 54 publications

Zinc Gallate Nanoplates on Microporous Organic Hollow Nanoplatforms for Enhanced Reductive CO2 Fixation to Formamides

Zinc Gallate Nanoplates on Microporous Organic Hollow Nanoplatforms for Enhanced Reductive CO2 Fixation to Formamides

Highly Efficient Thiolate‐Based Ionic Liquid Catalysts for Reduction of CO2: Selective N‐Functionalization of Amines to Form N‐Formamides and N‐Methylamines

One-pot two-step reduction of CO2 with amines and NaBH4 to N-substituted compounds at atmospheric pressure

Contact Info

Product

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Zinc Gallate Nanoplates on Microporous Organic Hollow Nanoplatforms for Enhanced Reductive CO₂ Fixation to Formamides

Zinc Gallate Nanoplates on Microporous Organic Hollow Nanoplatforms for Enhanced Reductive CO₂ Fixation to Formamides

Highly Efficient Thiolate‐Based Ionic Liquid Catalysts for Reduction of CO₂: Selective N‐Functionalization of Amines to Form N‐Formamides and N‐Methylamines