The synthesis of organic carbonates from carbon dioxide

Sakakura, Toshiyasu; Kohno, Kazufumi

doi:10.1039/b819997c

Cited by 1,018 publications

(540 citation statements)

References 156 publications

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“…[1] From a sustainability point of view, current processes for the synthesis of cyclic carbonates suffer from several disadvantages. They often involve harsh reaction conditions and unfavorable reagents, such as the highly toxic reagent phosgene.…”

Section: Introductionmentioning

confidence: 99%

Vanadium Catalyzed Synthesis of Cyclic Organic Carbonates

et al. 2012

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Vanadium complexes bearing easily synthesized, differently functionalized salen and salphen ligands were prepared and tested for their ability to catalyze the cycloaddition of carbon dioxide to epoxides resulting in cyclic organic carbonates. The reactivity of the prepared catalysts dramatically increases when a coordinating hydroxyl group is present as a substituent in the organic epoxide. The commercially available [VO(acac)2] complex was used as reference compound, and, in this case, we found that V10O26·(NBu4)4 was formed during the catalytic reactions. This compound, characterized by X-ray diffraction analysis, is likely the active catalyst, and it results in significantly better yields of cyclic carbonates compared to those obtained with Schiff base containing vanadyl complexes. The high activity of the mixed polyoxo vanadyl-vanadate complex\ud marks it as a powerful catalyst within the context of CO2 fixation chemistry

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Section: Introductionmentioning

confidence: 99%

Vanadium Catalyzed Synthesis of Cyclic Organic Carbonates

et al. 2012

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“…The utilization, as opposed to the storage of CO 2 , is indeed more attractive especially if the conversion process to useful bulk products is an economical one. Significant efforts have been devoted toward exploring technologies for CO 2 transformation, whereby harsh and severe reaction conditions are one of the major limitations for their practical applications (1)(2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15). Therefore, the development of efficient catalyst systems for CO 2 utilization under mild conditions is highly desired, especially for real world applications.…”

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confidence: 99%

“…T he chemical fixation and transformation of carbon dioxide (CO 2 ) has attracted much attention in view of environmental, legal, and social issues in the past few decades (1)(2)(3)(4)(5)(6)(7). Carbon dioxide is an attractive C1 building block in organic synthesis because it is an abundant, renewable carbon source and an environmentally friendly chemical reagent (8)(9)(10)(11)(12)(13).…”

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confidence: 99%

Copper- and copper– N -heterocyclic carbene-catalyzed C─H activating carboxylation of terminal alkynes with CO ₂ at ambient conditions

Zhang

2010

Proc. Natl. Acad. Sci. U.S.A.

272

121

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The use of carbon dioxide as a renewable and environmentally friendly source of carbon in organic synthesis is a highly attractive approach, but its real world applications remain a great challenge. The major obstacles for commercialization of most current protocols are their low catalytic performances, harsh reaction conditions, and limited substrate scope. It is important to develop new reactions and new protocols for CO 2 transformations at mild conditions and in cost-efficient ways. Herein, a copper-catalyzed and copper-N-heterocyclic carbene-cocatalyzed transformation of CO 2 to carboxylic acids via C─H bond activation of terminal alkynes with or without base additives is reported. Various propiolic acids were synthesized in good to excellent yields under ambient conditions without consumption of any organometallic or organic reagent additives. This system has a wide scope of substrates and functional group tolerances and provides a powerful tool for the synthesis of highly functionalized propiolic acids. This catalytic system is a simple and economically viable protocol with great potential in practical applications.

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“…One of the more successful processes for CO 2 utilization for material synthesis is the catalytic productions of cyclic carbonates and polycarbonates from epoxides 8 , which has been industrialized as well 9 . Nowadays, cyclic carbonates are widely used as organic synthetic intermediates, aprotic polar solvents, precursors for biomedical applications and raw materials for engineering plastics.…”

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confidence: 99%

Using carbon dioxide as a building block in organic synthesis

et al. 2015

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Carbon dioxide exits in the atmosphere and is produced by the combustion of fossil fuels, the fermentation of sugars and the respiration of all living organisms. An active goal in organic synthesis is to take this carbon-trapped in a waste product-and re-use it to build useful chemicals. Recent advances in organometallic chemistry and catalysis provide effective means for the chemical transformation of CO 2 and its incorporation into synthetic organic molecules under mild conditions. Such a use of carbon dioxide as a renewable one-carbon (C1) building block in organic synthesis could contribute to a more sustainable use of resources.A more sensible resource management is the prerequisite for the sustainable development of future generations. However, when dealing with the feedstock of the chemical industry, the level of sustainability is still far from satisfactory. Until now, the vast majority of carbon resources are based on crude oil, natural gas and coal. In addition to biomass, CO 2 offers the possibility to create a renewable carbon economy. Since pre-industrial times, the amount of CO 2 has steadily increased and nowadays CO 2 is a component of greenhouse gases, which are primarily responsible for the rise in atmospheric temperature and probably abnormal changes in the global climate. This increase in CO 2 concentration is largely due to the combustion of fossil fuels, which are required to meet the world's energy demand 1 . Obviously, there is an urgent need to control CO 2 emissions and develop efficient carbon capture systems. Although the extensive use of carbon dioxide for chemical production cannot solve this problem alone, CO 2 is a useful one-carbon (C1) building block in organic synthesis due to its abundance, availability, nontoxicity and recyclability. As a result, valorization of CO 2 is currently receiving considerable and ever increasing attention by the scientific community 2-4 . However, activation and utilization of CO 2 is still problematic due to the fact that it is the most oxidized form of carbon, which is also thermodynamically stable and/or kinetically inert in certain desired transformations. Consequently, most of the known studies used highly reactive substrates and/or severe reaction conditions to activate CO 2 , limiting the application of such methods. In particular, the catalytic coupling of CO 2 with energy-rich substrates, such as epoxides and aziridines, to generate polycarbonates/polycarbamates and/or cyclic carbonates/carbamates has drawn significant attention over the past decades. To create C-C bonds with CO 2 , the use of carbon nucleophiles is specifically limited to strong nucleophilic organolithiums and Grignard reagents, as well as phenolates.

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The synthesis of organic carbonates from carbon dioxide

Cited by 1,018 publications

References 156 publications

Vanadium Catalyzed Synthesis of Cyclic Organic Carbonates

Vanadium Catalyzed Synthesis of Cyclic Organic Carbonates

Copper- and copper– N -heterocyclic carbene-catalyzed C─H activating carboxylation of terminal alkynes with CO ₂ at ambient conditions

Using carbon dioxide as a building block in organic synthesis

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The synthesis of organic carbonates from carbon dioxide

Cited by 1,018 publications

References 156 publications

Vanadium Catalyzed Synthesis of Cyclic Organic Carbonates

Vanadium Catalyzed Synthesis of Cyclic Organic Carbonates

Copper- and copper– N -heterocyclic carbene-catalyzed C─H activating carboxylation of terminal alkynes with CO 2 at ambient conditions

Using carbon dioxide as a building block in organic synthesis

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Copper- and copper– N -heterocyclic carbene-catalyzed C─H activating carboxylation of terminal alkynes with CO ₂ at ambient conditions