Advancements in oxazolidinone synthesis utilizing carbon dioxide as a C1 source

Pulla, Sharon; Felton, Charlette M.; Ramidi, Punnamchandar; Gartia, Yashraj; Ali, Nawab; Nasini, Udaya B.; Ghosh, Anindya

doi:10.1016/j.jcou.2013.07.005

Cited by 95 publications

(41 citation statements)

References 44 publications

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“…A variety of comprehensive reviews on catalytic synthesis of organic molecules from CO2 have emerged in recent years, including metalbased and organic catalysis. 4,5,6,11,18,19,20,21,22,23,24,25,26,27,28 There are two catalytic approaches that have found widespread use for activation of the rather inert CO2 molecule (Scheme 1); both approaches involve incorporation of the entire CO2 molecule, which is our main focus here. In the first approach (Scheme 1a), C-CO2 bonds are primarily formed through insertion of CO2 into reactive metal-carbon bonds; in these reactions CO2 acts as an electrophile.…”

Section: Strategies For Bond Formation To Co2mentioning

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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Section: Strategies For Bond Formation To Co2mentioning

confidence: 99%

Enantioselective Incorporation of CO₂: Status and Potential

et al. 2017

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“…Although it is challenging to activate and utilize CO 2 owing to its thermodynamic stability and kinetical inertness, a variety of efficient CO 2 transformations have been discovered in the past decades . In addition to transformations in the presence of reductants, various kinds of non‐reductive processes have been realized to generate organic carboxylates,– (poly)carbonates,, carbamates/oxazolidinones, ureas, and lactones . Notably, the leading groups of Nolan and Cazin,– Hou,– and Iwasawa,, as well as others,– have reported elegant progress toward the direct carboxylation and lactonization of sp 2 C−H bonds, which are highly attractive owing to the high step‐ and atom‐economy.…”

Section: Figurementioning

confidence: 99%

Lactamization of sp² C−H Bonds with CO₂: Transition‐Metal‐Free and Redox‐Neutral

et al. 2016

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The first direct use of carbon dioxide in the lactamization of alkenyl and heteroaryl C−H bonds to synthesize important 2‐quinolinones and polyheterocycles in moderate to excellent yields is reported. Carbon dioxide, a nontoxic, inexpensive, and readily available greenhouse gas, acts as an ideal carbonyl source. Importantly, this transition‐metal‐free and redox‐neutral process is eco‐friendly and desirable for the pharmaceutical industry. Moreover, these reactions feature a broad substrate scope, good functional group tolerance, facile scalability, and easy product derivatization.

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“…Organic and inorganic salts, metal complexes, and ionic liquids have proven to be efficient homogeneous catalysts for this reaction. [148] Polymer-supported ionic liquids were also investigated with the aim of circumventing difficulties in separating and recovering the catalyst from the reaction medium. [149,150] The observed beneficial synergy during the synthesis of diethylcarbonate prompted Park et al to investigate the potential use of functionalized chitosan as an organocatalyst for the synthesis of oxazolidinone.…”

Section: Oxazolidinone Synthesismentioning

confidence: 99%

Chitosan as a Sustainable Organocatalyst: A Concise Overview

Kadib

2014

ChemSusChem

203

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Increased demand for more sustainable materials and chemical processes has tremendously advanced the use of polysaccharides, which are natural biopolymers, in domains such as adsorption, catalysis, and as an alternative chemical feedstock. Among these biopolymers, the use of chitosan, which is obtained by deacetylation of natural chitin, is on the increase due to the presence of amino groups on the polymer backbone that makes it a natural cationic polymer. The ability of chitosan-based materials to form open-network, macroporous, high-surface-area hydrogels with accessible basic surface sites has enabled their use not only as macrochelating ligands for active metal catalysts and as a support to disperse nanosized particles, but also as a direct organocatalyst. This review provides a concise overview of the use of native and modified chitosan, possessing different textural properties and chemical properties, as organocatalysts. Organocatalysis with chitosan is primarily focused on carbon-carbon bond-forming reactions, multicomponent heterocycle formation reactions, biodiesel production, and carbon dioxide fixation through [3+2] cycloaddition. Furthermore, the chiral, helical organization of the chitosan skeleton lends itself to use in enantioselective catalysis. Chitosan derivatives generally display reactivity similar to homogeneous bases, ionic liquids, and organic and inorganic salts. However, the introduction of cooperative acid-base interactions at active sites substantially enhances reactivity. These functional biopolymers can also be easily recovered and reused several times under solvent-free conditions. These accomplishments highlight the important role that natural biopolymers play in furthering more sustainable chemistry.

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Advancements in oxazolidinone synthesis utilizing carbon dioxide as a C1 source

Cited by 95 publications

References 44 publications

Enantioselective Incorporation of CO₂: Status and Potential

Enantioselective Incorporation of CO₂: Status and Potential

Lactamization of sp² C−H Bonds with CO₂: Transition‐Metal‐Free and Redox‐Neutral

Chitosan as a Sustainable Organocatalyst: A Concise Overview

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Advancements in oxazolidinone synthesis utilizing carbon dioxide as a C1 source

Cited by 95 publications

References 44 publications

Enantioselective Incorporation of CO2: Status and Potential

Enantioselective Incorporation of CO2: Status and Potential

Lactamization of sp2 C−H Bonds with CO2: Transition‐Metal‐Free and Redox‐Neutral

Chitosan as a Sustainable Organocatalyst: A Concise Overview

Contact Info

Product

Resources

About

Enantioselective Incorporation of CO₂: Status and Potential

Enantioselective Incorporation of CO₂: Status and Potential

Lactamization of sp² C−H Bonds with CO₂: Transition‐Metal‐Free and Redox‐Neutral