Zinc (II) incorporated porous organic polymeric material (POPs): A mild and efficient catalyst for synthesis of dicoumarols and carboxylative cyclization of propargyl alcohols and CO2 in ambient conditions

Salam, Noor; Molla, Rostam Ali; Riyajuddin, Sk; Yasmin, Nasima; Ghosh, Kaushik

doi:10.1016/j.mcat.2019.110541

Cited by 20 publications

(7 citation statements)

References 77 publications

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“…Accordingly, the center of carbon is much susceptible to nucleophilic attack (e.g., the O atom of propargylic alcohol activated by the DBU base can interact with the carbon center of CO 2 ), while the oxygen center can interact with electrophiles (e.g., activated alkyne moiety). After the nucleophilic attack by the O center of CO 2 , bond formation occurs between zinc species and alkyne part of the possible intermediate. ,− The adduct is proved to be advantageous for the incorporation of carbon dioxide to create the carbamate salt. Then, an intramolecular cyclization occurs, which affords the desired α-alkylidene cyclic carbonate product following the liberation of the Zn@RIO-1 catalyst.…”

Section: Resultsmentioning

confidence: 99%

“…Due to the aforesaid boundaries of previous reports, some developments are still required for the efficient production of α-alkylidene cyclic carbonates under suitable reaction conditions. Recently, our group published a catalytic protocol, where a porous organic polymer-based zinc metal catalyst is used for the synthesis of α-alkylidene cyclic carbonates at room temperature (RT) under solvent-free heterogeneous medium from carbon dioxide and propargylic alcohols . However, the protocol has a limitation of use under 1 MPa of CO 2 pressure.…”

Section: Introductionmentioning

confidence: 99%

“…Recently, our group published a catalytic protocol, where a porous organic polymer-based zinc metal catalyst is used for the synthesis of α-alkylidene cyclic carbonates at room temperature (RT) under solvent-free heterogeneous medium from carbon dioxide and propargylic alcohols. 24 However, the protocol has a limitation of use under 1 MPa of CO 2 pressure. In this article, we present a nanoporous covalent organic framework (COF)-assisted zinc metal catalyst, which efficiently produced α-alkylidene cyclic carbonates from CO 2 and propargylic alcohols under 1 atm pressure at RT and solvent-free conditions.…”

Section: Introductionmentioning

confidence: 99%

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Zn(II)-Embedded Nanoporous Covalent Organic Frameworks for Catalytic Conversion of CO₂ under Solvent-Free Conditions

Haque

Biswas

Ghosh

et al. 2021

ACS Appl. Nano Mater.

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Covalent organic frameworks (COFs) have been gaining substantial attention over the past decade due to their developing crystalline porous polymeric nature linked by strong covalent bonds and widespread applications in various fields. Currently, three-dimensional COFs (3D COFs) are engaging the spotlight due to their distinctive porous features, greater surface area, and exceptional performances in comparison with formerly published two-dimensional (2D) frameworks with the AA-stacking layered mode. In this paper, we present, for the first time, a nanoporous 3D-COF-based zinc(II) catalyst (Zn@RIO-1), which shows an efficient pathway for the chemical conversion of carbon dioxide to produce α-alkylidene cyclic carbonates and oxazolidinones from propargylic alcohols. The microporous material with a high surface area (312.61 m2/g) facilitates both types of catalytic reactions under atmospheric CO2 pressure. More importantly, easily recyclable and reusable catalysts produced moderate to high yields of desired carbonates as well as oxazolidinone products under solvent-free conditions. This study emphasizes the capability of nanoporous 3D-COF-based material in the catalysis field, more specifically in the field of CO2 capture and chemical fixation to fine chemicals. These results pave a spectacular pathway for the chemical fixation of CO2 into α-alkylidene cyclic carbonates and oxazolidinones from propargylic alcohols using 3D-COF as a potential heterogeneous ligand under sustainable conditions (i.e., solvent-free).

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Zn(II)-Embedded Nanoporous Covalent Organic Frameworks for Catalytic Conversion of CO₂ under Solvent-Free Conditions

Haque

Biswas

Ghosh

et al. 2021

ACS Appl. Nano Mater.

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“…Zinc catalyst. Ma et al reported on the only zinc-based catalysts that provided good efficiency when associated with TEA for the carboxylative cyclization of terminal tertiary propargylic alcohols [123,124]. The ZnI 2 /NEt 3 binary catalyst operated at low temperature (30 • C) and 1 MPa of CO 2 and provided the desired cyclic carbonate scaffolds.…”

Section: Synthesis Of Cyclic Carbonates From Propargylic Alcoholsmentioning

confidence: 99%

En Route to CO2-Based (a)Cyclic Carbonates and Polycarbonates from Alcohols Substrates by Direct and Indirect Approaches

et al. 2022

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This review is dedicated to the state-of-the art routes used for the synthesis of CO2-based (a)cyclic carbonates and polycarbonates from alcohol substrates, with an emphasis on their respective main advantages and limitations. The first section reviews the synthesis of organic carbonates such as dialkyl carbonates or cyclic carbonates from the carbonation of alcohols. Many different synthetic strategies have been reported (dehydrative condensation, the alkylation route, the “leaving group” strategy, the carbodiimide route, the protected alcohols route, etc.) with various substrates (mono-alcohols, diols, allyl alcohols, halohydrins, propargylic alcohols, etc.). The second section reviews the formation of polycarbonates via the direct copolymerization of CO2 with diols, as well as the ring-opening polymerization route. Finally, polycondensation processes involving CO2-based dimethyl and diphenyl carbonates with aliphatic and aromatic diols are described.

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“…Other Cu I or Zn II metal-anchored polymer catalysts, such as (dimethylamino)methyl-polystyrene-supported copper(I) iodide (DMAM-PS-CuI, 22) [76] and ZnI 2 -grafted benzene-benzylamine porous organic polymers (Zn@BBA-PA, 23), [77] have been also employed as heterogeneous catalysts. 22 afforded DMACC with a 97 % yield under supercritical conditions (T = 40 °C, p CO 2 = 100 bar) within 24 h at 8 mol% loading of CuI.…”

Section: Heterogeneous Catalysts Containing Metal-n Chelatesmentioning

confidence: 99%

Exovinylene Cyclic Carbonates: Multifaceted CO₂‐Based Building Blocks for Modern Chemistry and Polymer Science

2022

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Carbon dioxide is a renewable, inexhaustible, and cheap alternative to fossil resources for the production of fine chemicals and plastics. It can notably be converted into exovinylene cyclic carbonates, unique synthons gaining momentum for the preparation of an impressive range of important organic molecules and functional polymers, in reactions proceeding with 100 % atom economy under mild operating conditions in most cases. This Review summarizes the recent advances in their synthesis with particular attention on describing the catalysts needed for their preparation and discussing the unique reactivity of these CO2‐based heterocycles for the construction of diverse organic building blocks and (functional) polymers. We also discuss the challenges and the future perspectives in the field.

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Zinc (II) incorporated porous organic polymeric material (POPs): A mild and efficient catalyst for synthesis of dicoumarols and carboxylative cyclization of propargyl alcohols and CO2 in ambient conditions

Cited by 20 publications

References 77 publications

Zn(II)-Embedded Nanoporous Covalent Organic Frameworks for Catalytic Conversion of CO₂ under Solvent-Free Conditions

Zn(II)-Embedded Nanoporous Covalent Organic Frameworks for Catalytic Conversion of CO₂ under Solvent-Free Conditions

En Route to CO2-Based (a)Cyclic Carbonates and Polycarbonates from Alcohols Substrates by Direct and Indirect Approaches

Exovinylene Cyclic Carbonates: Multifaceted CO₂‐Based Building Blocks for Modern Chemistry and Polymer Science

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Zinc (II) incorporated porous organic polymeric material (POPs): A mild and efficient catalyst for synthesis of dicoumarols and carboxylative cyclization of propargyl alcohols and CO2 in ambient conditions

Cited by 20 publications

References 77 publications

Zn(II)-Embedded Nanoporous Covalent Organic Frameworks for Catalytic Conversion of CO2 under Solvent-Free Conditions

Zn(II)-Embedded Nanoporous Covalent Organic Frameworks for Catalytic Conversion of CO2 under Solvent-Free Conditions

En Route to CO2-Based (a)Cyclic Carbonates and Polycarbonates from Alcohols Substrates by Direct and Indirect Approaches

Exovinylene Cyclic Carbonates: Multifaceted CO2‐Based Building Blocks for Modern Chemistry and Polymer Science

Contact Info

Product

Resources

About

Zn(II)-Embedded Nanoporous Covalent Organic Frameworks for Catalytic Conversion of CO₂ under Solvent-Free Conditions

Zn(II)-Embedded Nanoporous Covalent Organic Frameworks for Catalytic Conversion of CO₂ under Solvent-Free Conditions

Exovinylene Cyclic Carbonates: Multifaceted CO₂‐Based Building Blocks for Modern Chemistry and Polymer Science