Palladium-catalyzed incorporation of atmospheric CO<sub>2</sub>: efficient synthesis of functionalized oxazolidinones

García-Domínguez, Patricia; Fehr, Lorenz; Rusconi, Giulia; Nevado, Cristina

doi:10.1039/c6sc00419a

Cited by 108 publications

(53 citation statements)

References 38 publications

(20 reference statements)

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“…In 2016, the Nevado group reported a palladium‐catalyzed three‐component reaction between propargylic amines, aryl iodides, and CO 2 (Scheme ) . A series of oxazolidin‐2‐ones that contained tetrasubstituted exocyclic C=C double bonds were readily accessed in a stereocontrolled fashion.…”

Section: Cyclization Reactions Of Propargylic Amines With Co2mentioning

confidence: 99%

Synthesis of Oxazolidin‐2‐ones from Unsaturated Amines with CO₂ by Using Homogeneous Catalysis

Zhang

et al. 2018

Chemistry An Asian Journal

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Carbon dioxide (CO ), a well-known greenhouse gas, is also a nontoxic, readily accessible, and renewable one-carbon (C1) source. However, owing to its thermodynamic stability and kinetic inertness, the efficient utilization of CO is challenging. Much effort has been devoted to achieving efficient and selective organic transformations of CO . Recently, the synthesis of important oxazolidin-2-ones from unsaturated amines by using CO has attracted much attention and been heavily studied. This Focus Review presents recent advances in this area by using homogenous catalysis. The cyclization of amines that contain alkynes, alkenes, and allenes with CO is discussed, and possible reaction mechanisms and applications of these transformations are also described.

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Section: Cyclization Reactions Of Propargylic Amines With Co2mentioning

confidence: 99%

Synthesis of Oxazolidin‐2‐ones from Unsaturated Amines with CO₂ by Using Homogeneous Catalysis

Zhang

et al. 2018

Chemistry An Asian Journal

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“…Mono-and diarylsubstituted oxazolidinones from propargylic amines and CO2. 95 Other interesting substrates have been used for oxazolidinone synthesis, but not enantioselectively. In 2014, Repo and coworkers 34 reported 5-and 6-membered cyclic carbamates from racemic cyclization of various β-and γ-haloamines with CO2, and Soldi et al 96 reported intramolecular carboxylative cyclization of allylamines.…”

Section: Scheme 19mentioning

confidence: 99%

“…93,94 Nevado and coworkers have reported a Pd-catalyzed carboxylation of propargylic amines and aryliodides, giving mono-arylated oxazolidinones with complete E-selectivity (Scheme 20). 95 Also homodiarylated (Ar 1 = Ar 2 ) and heterodiarylated products (Ar 1 ≠ Ar 2 ) can be obtained by changing the reactions conditions. Note that any chiral products were prepared as racemic mixtures only.…”

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confidence: 99%

Enantioselective Incorporation of CO₂: Status and Potential

et al. 2017

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CO2 is a promising and sustainable carbon feedstock for organic synthesis. New catalytic protocols for efficient incorporation of CO2 into organic molecules are continuously reported. However, little progress has been made in the enantioselective conversion of CO2 to form enantioenriched molecules. In order to allow CO2 to become a versatile carbon source in academia, and in the fine chemical and pharmaceutical industries, the development of enantioselective approaches is essential. Here we discuss general strategies for CO2 activation and for generation of enantioenriched molecules, alongside selected examples of reactions involving asymmetric incorporation of CO2. Main product classes considered are carboxylic acids and derivatives (C-2 CO2 bonds), and carbonates, carbamates, and polycarbonates (C-OCO bonds). Similarities to asymmetric hydrogenation are discussed, and some strategies for developing novel enantioselective CO2 reactions are outlined.

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“…Nevado et al. have employed Pd nanocatalysts for the synthesis of oxazolidinones from propargylamines, aryl halides, and CO 2 . However, often very high pressure of CO 2 is necessary to achieve a high conversion level.…”

Section: Future Potentialmentioning

confidence: 99%

Supported Porous Nanomaterials as Efficient Heterogeneous Catalysts for CO₂ Fixation Reactions

Bhanja

Modak

Bhaumik

2018

Chemistry A European J

113

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CO is a major greenhouse gas responsible for global warming and can act as an abundant and inexpensive C1 source for enhancing the chain length/functionalization of a wide range of reactive organic molecules. It is moderately reactive, nontoxic and renewable. Thus, CO fixation reactions are important to meet the global challenges, that is, to mitigate the concentration of CO in the atmosphere through its fruitful utilization, which is of great interest from economic and environmental perspectives. Various metallic nanoparticles as well as metal oxides can be supported over high surface area porous materials and the resulting nanomaterial can act as heterogeneous and reusable solid catalyst for CO fixation reactions for the synthesis of a large number of fuels, natural products agrochemicals, and pharmaceutical compounds. Here we present an overview of the recent progress as well as promising future of metal/metal oxide nanoparticles supported over porous nanomaterials as heterogeneous catalysts for a wide spectrum of these CO fixation reactions.

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Palladium-catalyzed incorporation of atmospheric CO₂: efficient synthesis of functionalized oxazolidinones

Abstract: CO2 at atmospheric pressure is used in two Pd-catalyzed multicomponent reactions to produce functionalized 5-methylene-1,3-oxazolidin-2-ones from propargylamines and aryl halides.

Cited by 108 publications

References 38 publications

Synthesis of Oxazolidin‐2‐ones from Unsaturated Amines with CO₂ by Using Homogeneous Catalysis

Synthesis of Oxazolidin‐2‐ones from Unsaturated Amines with CO₂ by Using Homogeneous Catalysis

Enantioselective Incorporation of CO₂: Status and Potential

Supported Porous Nanomaterials as Efficient Heterogeneous Catalysts for CO₂ Fixation Reactions

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Palladium-catalyzed incorporation of atmospheric CO2: efficient synthesis of functionalized oxazolidinones

Abstract: CO2 at atmospheric pressure is used in two Pd-catalyzed multicomponent reactions to produce functionalized 5-methylene-1,3-oxazolidin-2-ones from propargylamines and aryl halides.

Cited by 108 publications

References 38 publications

Synthesis of Oxazolidin‐2‐ones from Unsaturated Amines with CO2 by Using Homogeneous Catalysis

Synthesis of Oxazolidin‐2‐ones from Unsaturated Amines with CO2 by Using Homogeneous Catalysis

Enantioselective Incorporation of CO2: Status and Potential

Supported Porous Nanomaterials as Efficient Heterogeneous Catalysts for CO2 Fixation Reactions

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Product

Resources

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Palladium-catalyzed incorporation of atmospheric CO₂: efficient synthesis of functionalized oxazolidinones

Synthesis of Oxazolidin‐2‐ones from Unsaturated Amines with CO₂ by Using Homogeneous Catalysis

Synthesis of Oxazolidin‐2‐ones from Unsaturated Amines with CO₂ by Using Homogeneous Catalysis

Enantioselective Incorporation of CO₂: Status and Potential

Supported Porous Nanomaterials as Efficient Heterogeneous Catalysts for CO₂ Fixation Reactions