On the direct use of CO<sub>2</sub>in multicomponent reactions: introducing the Passerini four component reaction

Onwukamike, Kelechukwu N.; Grelier, Stéphane; Grau, Étienne; Cramail, Henri; Meier, Michael A. R.

doi:10.1039/c8ra07150k

Cited by 7 publications

(3 citation statements)

References 36 publications

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“…Further investigations concerning the solubility is needed. Additionally, the synthesis procedure itself might be improved, by applying a switchable solvent system, which was recently introduced in the Passerini‐four‐component reaction . In this way, higher yields and enhanced DS might be obtained.…”

Section: Methodsmentioning

confidence: 99%

A Direct One‐Pot Modification of β‐Cyclodextrin via the Ugi‐Five‐Component Reaction

2020

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Starch‐derived β‐cyclodextrins (β‐CDs) are used in pharmacy or the food and cosmetic industry as drug deliverers, separating agents, catalysts, detergents, or viscosity modifiers. However, solubility issues often restrict their potential applications. Here, we report a straightforward and direct one‐pot synthesis for the modification of β‐CDs based on the Ugi‐five‐component reaction (Ugi‐5CR). The Ugi‐5CR requires to react an amine, an aldehyde, an isocyanide, carbon dioxide and the β‐CD, which serves as alcohol component. Overall, five modified β‐CDs containing carbamate moieties were synthesized at room temperature in a high pressure reactor (10 bar) within 24 hours. The successful modifications are verified by mass spectrometry, nuclear magnetic resonance, and infrared spectroscopy, indicating one to three reacted primary hydroxyl groups per β‐CD. Additionally, we report altered solubility behavior of two of the five modified β‐CDs.

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Section: Methodsmentioning

confidence: 99%

A Direct One‐Pot Modification of β‐Cyclodextrin via the Ugi‐Five‐Component Reaction

2020

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“…Cramail and Meier 67 have reported the Passerini four-component reaction between aldehydes, isocyanides, alcohols and carbon dioxide. The reaction proceeds through the formation of a carbonate ion, initiated by a base catalyst, and its attack on the nitrilium ion, followed by Mumm's rearrangement of intermediate 99 and formation of an α-alkoxycarbonyl amide 100 ( Scheme 30 ).…”

Section: New Opportunities For the Passerini Reaction By The Replacement Of One Or Two Componentsmentioning

confidence: 99%

The 100 facets of the Passerini reaction

et al. 2021

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“…We were able to achieve complete cellulose solubilization within 10-15 min at 30°C under very low CO 2 pressure (2-5 bar). Such mild solubilization conditions allowed us to explore this switchable solvent system to show a more sustainable succinylation of cellulose, (Söyler et al 2018) transesterification of cellulose using plant oils directly, (Onwukamike et al 2018c) and in multicomponent reaction, in which the CO 2 was employed as a C1-carbon source (Onwukamike et al 2018b). In addition, we employed this solvent system to produce cellulose aerogels with porosity higher than 95 % (Onwukamike et al 2019).…”

Section: Introductionmentioning

confidence: 99%

Direct electrospinning of cellulose in the DBU-CO2 switchable solvent system

et al. 2021

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We report the use of the DBU-CO2 switchable solvent system for the direct electrospinning of cellulose. Two cellulose types were investigated, i.e. microcrystalline cellulose (MCC) and cellulose pulp (CP). The morphologies of the obtained cellulose fibers were studied using scanning electron microscopy and optical microscopy. Results obtained showed that only particles with mean diameter about 1.2 μm could be obtained when MCC was used, even at high concentration (10 wt%). In the case of CP, an optimized concentration of 4 wt% resulted in standing fibers with a mean diameter of about 500nm. In order to improve the spinnability of the cellulose, different concentrations and ratios of PVA in combination with cellulose were investigated. The combination of cellulose (both MCC and CP) resulted in the formation of a unique fiber morphology, characterized by a homogeneous bead-like structure. An in-depth study of the fiber structure was carried out using Raman spectroscopy and showed that both cellulose and PVA were present in the formed beads. Finally, the challenge observed remained a complete removal of the solvents, which are not volatile enough, as well as explore a coagulation collection process for the fiber recovery in order to recover and re-use the employed solvent. Graphic abstract

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On the direct use of CO₂in multicomponent reactions: introducing the Passerini four component reaction

Abstract: We introduce a novel isocyanide-based multicomponent reaction, the Passerini four component reaction (P-4CR), by replacing the carboxylic acid component of a conventional Passerini three component reaction (P-3CR) with an alcohol and CO2.

Cited by 7 publications

References 36 publications

A Direct One‐Pot Modification of β‐Cyclodextrin via the Ugi‐Five‐Component Reaction

A Direct One‐Pot Modification of β‐Cyclodextrin via the Ugi‐Five‐Component Reaction

The 100 facets of the Passerini reaction

Direct electrospinning of cellulose in the DBU-CO2 switchable solvent system

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On the direct use of CO2in multicomponent reactions: introducing the Passerini four component reaction

Abstract: We introduce a novel isocyanide-based multicomponent reaction, the Passerini four component reaction (P-4CR), by replacing the carboxylic acid component of a conventional Passerini three component reaction (P-3CR) with an alcohol and CO2.

Cited by 7 publications

References 36 publications

A Direct One‐Pot Modification of β‐Cyclodextrin via the Ugi‐Five‐Component Reaction

A Direct One‐Pot Modification of β‐Cyclodextrin via the Ugi‐Five‐Component Reaction

The 100 facets of the Passerini reaction

Direct electrospinning of cellulose in the DBU-CO2 switchable solvent system

Contact Info

Product

Resources

About

On the direct use of CO₂in multicomponent reactions: introducing the Passerini four component reaction