Transition metal complex catalyzed carboxylation reactions with CO2

Yu, Dingyi; Teong, Siew Ping; Zhang, Yugen

doi:10.1016/j.ccr.2014.09.002

Cited by 225 publications

(66 citation statements)

References 121 publications

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“…6,20,22,56 Here we give examples of diverse carboxylic acids formed in an enantioenriched manner from CO2.…”

Section: Examples Of Asymmetric C-co2 Bond Formationmentioning

confidence: 99%

“…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%

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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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“…6,20,22,56 Here we give examples of diverse carboxylic acids formed in an enantioenriched manner from CO2.…”

Section: Examples Of Asymmetric C-co2 Bond Formationmentioning

confidence: 99%

Section: Strategies For Bond Formation To Co2mentioning

confidence: 99%

Enantioselective Incorporation of CO₂: Status and Potential

et al. 2017

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“…In fact, more than 110 megatons of CO 2 are used annually in industry for the synthesis of urea, salicylic acid, and carbonates [1,5]. However, CO 2 is a highly oxidized and thermodynamically stable gas and, consequently, high activation energies are required for its functionalization [6][7][8][9][10].…”

Section: Introductionmentioning

confidence: 99%

Ni- and Fe-catalyzed Carboxylation of Unsaturated Hydrocarbons with CO2

et al. 2016

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The sustainable utilization of available feedstock materials for preparing valuable compounds holds great promise to revolutionize approaches in organic synthesis. In this regard, the implementation of abundant and inexpensive carbon dioxide (CO2) as a C1 building block has recently attracted considerable attention. Among the different alternatives in CO2 fixation, the preparation of carboxylic acids, relevant motifs in pharmaceuticals and agrochemicals, is particularly appealing, thus providing a rapid and unconventional entry to building blocks that are typically prepared via waste-producing protocols. While significant advances have been realized, the utilization of simple unsaturated hydrocarbons as coupling partners in carboxylation events is undoubtedly of utmost academic and industrial relevance, as two available feedstock materials can be combined in a catalytic fashion. This review article aims to describe the main achievements on the direct carboxylation of unsaturated hydrocarbons with CO2 by using cheap and available Ni or Fe catalytic species.

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“…The authors suggest a key role could be played at this stage by the oxygen donor atom of Xantphos ligand as its coordination to Co would assist the tautomerization of η 3 -allyl-Co to η 1 -allyl-Co complex (Scheme 13b). Reductive elimination of CH 4 from η 1 -allyl-Co(H)(CH 3 ) intermediate (13) leads to a low valent allyl-Co complex (14) able to undergo electrophilic attack from CO 2 at the γ-position. The last stage involves transmetallation between the carboxylated-Co complex (15) and AlMe 3 regenerating the L n Co(I)Me catalyst and producing R-COOAlMe 2 .…”

Section: Carboxylation Of Benzylic and Allylic C(sp 3 )-H Bonds Catalmentioning

confidence: 99%

“…The high thermal and kinetic stability of the CO 2 molecule require for a suitable catalyst and energy input when employed in E-CO 2 bond formation (E = O, N, C) or reduction reactions. Current synthetic options for CO 2 -fixation into useful chemicals encompasses chemical, electro-chemical, photo-chemical, photo-electrochemical and biological approach that have been overviewed in a number of excellent books and comprehensive reviews [2][3][4][5][6][7][8][9][10][11][12][13][14][15][16][17].…”

Section: Introductionmentioning

confidence: 99%

Direct Carboxylation of C(sp3)-H and C(sp2)-H Bonds with CO2 by Transition-Metal-Catalyzed and Base-Mediated Reactions

Tommasi

2017

Catalysts

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This review focuses on recent advances in the field of direct carboxylation reactions of C(sp 3 )-H and C(sp 2 )-H bonds using CO 2 encompassing both transition-metal-catalysis and base-mediated approach. The review is not intended to be comprehensive, but aims to analyze representative examples from the literature, including transition-metal catalyzed carboxylation of benzylic and allylic C(sp 3 )-H functionalities using CO 2 which is at a "nascent stage". Examples of light-driven carboxylation reactions of unactivated C(sp 3 )-H bonds are also considered. Concerning C(sp 3 )-H and C(sp 2 )-H deprotonation reactions mediated by bases with subsequent carboxylation of the carbon nucleophile, few examples of catalytic processes are reported in the literature. In spite of this, several examples of base-promoted reactions integrating "base recycling" or "base regeneration (through electrosynthesis)" steps have been reported. Representative examples of synthetically efficient, base-promoted processes are included in the review.

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Transition metal complex catalyzed carboxylation reactions with CO2

Cited by 225 publications

References 121 publications

Enantioselective Incorporation of CO₂: Status and Potential

Enantioselective Incorporation of CO₂: Status and Potential

Ni- and Fe-catalyzed Carboxylation of Unsaturated Hydrocarbons with CO2

Direct Carboxylation of C(sp3)-H and C(sp2)-H Bonds with CO2 by Transition-Metal-Catalyzed and Base-Mediated Reactions

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Transition metal complex catalyzed carboxylation reactions with CO2

Cited by 225 publications

References 121 publications

Enantioselective Incorporation of CO2: Status and Potential

Enantioselective Incorporation of CO2: Status and Potential

Ni- and Fe-catalyzed Carboxylation of Unsaturated Hydrocarbons with CO2

Direct Carboxylation of C(sp3)-H and C(sp2)-H Bonds with CO2 by Transition-Metal-Catalyzed and Base-Mediated Reactions

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Enantioselective Incorporation of CO₂: Status and Potential

Enantioselective Incorporation of CO₂: Status and Potential