Microwave-Assisted, Green Synthesis of 4(3<i>H</i>)-Quinazolinones under CO Pressure in γ-Valerolactone and Reusable Pd/β-Cyclodextrin Cross-Linked Catalyst

Gaudino, Emanuela Calcio; Tagliapietra, Silvia; Palmisano, Giovanni; Martina, Katia; Carnaroglio, Diego; Cravotto, Giancarlo

doi:10.1021/acssuschemeng.7b02193

Cited by 22 publications

(8 citation statements)

References 46 publications

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“…Our group have recently synthesized a new class of heterogeneous Pd catalysts that are supported on a β-cyclodextrin (β-CD) crosslinked network (the Pd/CβCAT system) [44,45], via the sonochemical reticulation of β-cyclodextrin with hexamethylene diisocyanate (HDI) in the presence of a Pd(II) salt solution [46]. The cheaper and available in bulk β-CD, was preferred to α- and γ-CD because of the comparable catalytic effect already documented in cross-linked CD catalysts.…”

Section: Introductionmentioning

confidence: 99%

“…Intermolecular cavities and cross-linking degree strongly affect the catalytic process and metal leaching, minimizing the role of cyclodextrins’ inner cavities size. This Pd/CβCAT catalyst has proven to be particularly efficient in the absorption of MW irradiation, making it an ideal candidate for the synergic combination of the non-conventional enabling technology and heterogeneous catalysis [45,47].…”

Section: Introductionmentioning

confidence: 99%

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Microwave-Assisted Dehydrogenative Cross Coupling Reactions in γ-valerolactone with a Reusable Pd/β-cyclodextrin Crosslinked Catalyst

et al. 2019

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Transition-metal mediated C–H bond activation and functionalization is one of the most straightforward and powerful tools in modern organic synthetic chemistry. Oxidative C–H/C–H coupling reactions between two (hetero)arenes under heterogeneous catalysis may be a valuable means for the production of a plethora of bi(hetero)aryls, and one that adheres to the increasing demand for atom-economic and sustainable chemistry. We have therefore developed a reusable heterogeneous catalytic system, which is based on Pd cross-linked β-cyclodextrin, to perform an efficient microwave-assisted oxidative C–H/C–H cross coupling process between benzothiazoles and methyl thiophene in the presence of green solvents.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Microwave-Assisted Dehydrogenative Cross Coupling Reactions in γ-valerolactone with a Reusable Pd/β-cyclodextrin Crosslinked Catalyst

et al. 2019

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“…We have synthesized PSR‐supported Pd and Au NPs which were successfully applied to the MW‐assisted C−C coupling reactions under green and sustainable reaction conditions (Figure 7); 30 years of microwave explorations have documented a significant advantageous of MW heating in organic synthesis [65,66] Importantly, these MW‐assisted organic transformation exhibited a drastic decrease in the reaction times and increase in product selectivity [67,68] …”

Section: Catalytic Application Of Psr‐supported Nanocatalysts In Vari...mentioning

confidence: 99%

Polystyrene Resins: Versatile and Economical Support for Heterogeneous Nanocatalysts in Sustainable Organic Reactions**

Sharma

Yadav

et al. 2023

ChemCatChem

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Recent developments in heterogeneous nanocatalysis have illustrated the great strides metal nanoparticles (NPs) have made due to their several significant features. However, the major lingering challenge has been their deactivation in organic reactions by migration-coalescence largely due to their high surface energy. In this context, various supports materials have been designed to overcome the stability issues for metal NPs. Furthermore, the activity and selectivity could be simultaneously enhanced by taking advantage of the synergy between the metal NPs and the support material, like abundantly available inexpensive polystyrene resins (PSR). Herein, the recent developments on PSR-supported catalysts are deliberated for assorted organic reactions conducted under sustainable conditions. The salient advantageous attributes of nanocatalyst-adorned PSR are discussed in terms of their activity, recyclability, stability and selectivity for various organic transformations. Further, the enduring challenges associated with the PSR-supported nanocatalysts and future perspectives for further developments are explicated.

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“…In the search for more sustainable processes, nanostructured catalysts have been the subject of considerable academic and industrial research attention in recent times due to the numerous potential benefits related to their use (minimal chemical waste, and energy efficiency, among others). Despite exhibiting high catalytic activity and selectivity like homogeneous catalysis, the encapsulation of metal within a polymeric network renders the nanocatalyst recoverable, thus avoiding metal leaching [32,33]. Several metals loaded CβCAT were prepared by the reticulation of Pd/β-CD, Cu/β-CD, and PdCu/β-CD with hexamethylenediisocyanate (HDI), according to a previously documented procedure [34,35].…”

Section: Catalyst Preparation and Characterizationmentioning

confidence: 99%

Cross-Linked Cyclodextrins Bimetallic Nanocatalysts: Applications in Microwave-Assisted Reductive Aminations

et al. 2020

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The optimization of sustainable protocols for reductive amination has been a lingering challenge in green synthesis. In this context, a comparative study of different metal-loaded cross-linked cyclodextrins (CDs) were examined for the microwave (MW)-assisted reductive amination of aldehydes and ketones using either H2 or formic acid as a hydrogen source. The Pd/Cu heterogeneous nanocatalyst based on Pd (II) and Cu (I) salts embedded in a β-CD network was the most efficient in terms of yield and selectivity attained. In addition, the polymeric cross-linking avoided metal leaching, thus enhancing the process sustainability; good yields were realized using benzylamine under H2. These interesting findings were then applied to the MW-assisted one-pot synthesis of secondary amines via a tandem reductive amination of benzaldehyde with nitroaromatics under H2 pressure. The formation of a CuxPdy alloy under reaction conditions was discerned, and a synergic effect due to the cooperation between Cu and Pd has been hypothesized. During the reaction, the system worked as a bifunctional nanocatalyst wherein the Pd sites facilitate the reduction of nitro compounds, while the Cu species promote the subsequent imine hydrogenation affording structurally diverse secondary amines with high yields.

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Microwave-Assisted, Green Synthesis of 4(3H)-Quinazolinones under CO Pressure in γ-Valerolactone and Reusable Pd/β-Cyclodextrin Cross-Linked Catalyst

Cited by 22 publications

References 46 publications

Microwave-Assisted Dehydrogenative Cross Coupling Reactions in γ-valerolactone with a Reusable Pd/β-cyclodextrin Crosslinked Catalyst

Microwave-Assisted Dehydrogenative Cross Coupling Reactions in γ-valerolactone with a Reusable Pd/β-cyclodextrin Crosslinked Catalyst

Polystyrene Resins: Versatile and Economical Support for Heterogeneous Nanocatalysts in Sustainable Organic Reactions**

Cross-Linked Cyclodextrins Bimetallic Nanocatalysts: Applications in Microwave-Assisted Reductive Aminations

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