Recent Progress in the Cyclization Reactions Using Carbon Dioxide

Zhang, Wenzhen; Zhang, Ning; Guo, Cheng; Lu, Xiao‐Bing

doi:10.6023/cjoc201701031

Cited by 70 publications

(11 citation statements)

References 16 publications

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“…Chemical fixation of CO 2 into available chemicals and fuels has recently turned into one of the most fertile arenas in the field of industry and energy, which is in line with the view of sustainable development and environmental protection. − To date, more than 20 reactions involving CO 2 as a C1 feedstock have been intensively developed over the past decades. − In particular, the insertion of CO 2 into epoxides for affording cyclic carbonates has been proposed as a promising strategy for recycling carbon resource, not only because of its 100% atom economy but also on account of great industrial potential of cyclic carbonates. − So far, plenty of effort has been devoted to the development of efficient catalytic systems for this conversion, especially several metal-based systems with extremely high reactivity and selectivity such as metallosalen complexes − and metalloporphyrins. − On closer inspection of these catalytic systems have been reported so far, the dual electrophilic/nucleophilic behavior toward the activation of an epoxide has been widely accepted in this transformation (Scheme A). On the basis of this, the metal-based catalysts often need to combine with additional cocatalyst as a nucleophile to ensure their efficiency.…”

Section: Introductionmentioning

confidence: 97%

Metalloporphyrin Polymers with Intercalated Ionic Liquids for Synergistic CO₂ Fixation via Cyclic Carbonate Production

Chen

Luo

et al. 2017

ACS Sustainable Chem. Eng.

125

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Multifunctionalization of organic polymers for acting synergistically on substrate is of wide interest in the field of modern catalysis, but it is still a significant challenge. Herein, two novel bifunctional polymers were first designed and synthesized by combining ionic liquids (ILs) with zinc(II) porphyrin through simple and reversible Schiff base reactions. The fabricated polymers with flexible structures and nitrogen-rich environments presented high affinity toward CO 2 molecules at ambient conditions. Owing to the cooperative nature of intercalated ILs and Lewis acidic metal sites, these materials could serve as efficient heterogeneous catalysts for the insertion of CO 2 into epoxides to produce cyclic carbonates. As expected, these polymers exhibited good catalytic performance, robust constancy, excellent recyclability, and good substrate expansibility for this reaction in the absence of cocatalyst under mild or even ambient conditions. Notably, the selected catalyst SYSU-Zn@IL2 could directly convert diluted CO 2 (15% CO 2 in N 2 ) into cyclic carbonate at 80 °C and 3.0 MPa, further offering the great application potential for recycling real-world carbon resource.

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Section: Introductionmentioning

confidence: 97%

Metalloporphyrin Polymers with Intercalated Ionic Liquids for Synergistic CO₂ Fixation via Cyclic Carbonate Production

Chen

Luo

et al. 2017

ACS Sustainable Chem. Eng.

125

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“…With increasing attention on climate change, the fixation and transformation of carbon dioxide (CO 2 ), a greenhouse gas, has become a hot topic for chemical researchers . CO 2 is a one‐carbon (C 1 ) source that is nontoxic, nonflammable, renewable, abundant, and inexpensive.…”

Section: Introductionmentioning

confidence: 99%

C−H Bond Carboxylation with Carbon Dioxide

et al. 2019

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Carbon dioxide is a nontoxic, renewable, and abundant C1 source, whereas C−H bond functionalization represents one of the most important approaches to the construction of carbon–carbon bonds and carbon–heteroatom bonds in an atom‐ and step‐economical manner. Combining the chemical transformation of CO2 with C−H bond functionalization is of great importance in the synthesis of carboxylic acids and their derivatives. The contents of this Review are organized according to the type of C−H bond involved in carboxylation. The primary types of C−H bonds are as follows: C(sp)−H bonds of terminal alkynes, C(sp2)−H bonds of (hetero)arenes, vinylic C(sp2)−H bonds, the ipso‐C(sp2)−H bonds of the diazo group, aldehyde C(sp2)−H bonds, α‐C(sp3)−H bonds of the carbonyl group, γ‐C(sp3)−H bonds of the carbonyl group, C(sp3)−H bonds adjacent to nitrogen atoms, C(sp3)−H bonds of o‐alkyl phenyl ketones, allylic C(sp3)−H bonds, C(sp3)−H bonds of methane, and C(sp3)−H bonds of halogenated aliphatic hydrocarbons. In addition, multicomponent reactions, tandem reactions, and key theoretical studies related to the carboxylation of C−H bonds are briefly summarized. Transition‐metal‐free, organocatalytic, electrochemical, and light‐driven methods are highlighted.

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“…[2] Notably, the synthesis of heterocycles with CO 2 has received great attention. [3] Among a huge number of heterocycles, oxazinones are one kind of important motifs, which are common in drugs, bioactive natural products and key intermediates in organic synthesis. [4] Lots of methods have been reported to generate such structures.…”

Section: Introductionmentioning

confidence: 99%

Lactonization of C(sp²)—H Bonds in Enamides with CO₂

et al. 2018

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Herein, we report a novel synthesis of 1,3-oxazin-6-ones from enamides with CO 2 through C-H carboxylation and one-pot cyclization. This transition-metal-free and redox-neutral process features broad substrate scope, good functional group tolerance and facile product derivatization. The nucleophilic attack to CO 2 from the electron-rich alkene is demonstrated for this reaction.At the beginning, we made a lot of attempts based on previous reactions conditions and only detected the carboxylation products. As the cyclization products, 1,3-oxazin-6-ones, are highly important and can been easily obtained via cyclization in

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Recent Progress in the Cyclization Reactions Using Carbon Dioxide

Cited by 70 publications

References 16 publications

Metalloporphyrin Polymers with Intercalated Ionic Liquids for Synergistic CO₂ Fixation via Cyclic Carbonate Production

Metalloporphyrin Polymers with Intercalated Ionic Liquids for Synergistic CO₂ Fixation via Cyclic Carbonate Production

C−H Bond Carboxylation with Carbon Dioxide

Lactonization of C(sp²)—H Bonds in Enamides with CO₂

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Recent Progress in the Cyclization Reactions Using Carbon Dioxide

Cited by 70 publications

References 16 publications

Metalloporphyrin Polymers with Intercalated Ionic Liquids for Synergistic CO2 Fixation via Cyclic Carbonate Production

Metalloporphyrin Polymers with Intercalated Ionic Liquids for Synergistic CO2 Fixation via Cyclic Carbonate Production

C−H Bond Carboxylation with Carbon Dioxide

Lactonization of C(sp2)—H Bonds in Enamides with CO2

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Product

Resources

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Metalloporphyrin Polymers with Intercalated Ionic Liquids for Synergistic CO₂ Fixation via Cyclic Carbonate Production

Metalloporphyrin Polymers with Intercalated Ionic Liquids for Synergistic CO₂ Fixation via Cyclic Carbonate Production

Lactonization of C(sp²)—H Bonds in Enamides with CO₂