☆ 4.6 Review

Donor-Acceptor Activation of Carbon Dioxide

CHEMISTRY-A EUROPEAN JOURNAL (2023)

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Article Chemistry, Multidisciplinary

An Aluminum Telluride with a Terminal Al=Te Bond and its Conversion to an Aluminum Tellurocarbonate by CO2 Reduction

Huihui Xu et al.

Summary: Facile access to dimeric heavier aluminum chalcogenides [(NHC)Al(Tipp)-mu-Ch](2) (NHC=IiPr, IMe4; Tipp=2,4,6-iPr(3)C(6)H(2); Ch=Se, Te) by treatment of NHC-stabilized aluminum dihydrides with elemental Se and Te is reported. The higher affinity of IMe4 in comparison with IiPr toward the Al center in [(NHC)Al(Tipp)-mu-Ch](2) can be used for ligand exchange. Additionally, the presence of excess IMe4 allows for cleavage of the dimers to form a rare example of a neutral multiply bonded heavier aluminum chalcogenide in the form of a tetracoordinate aluminum complex, (IMe4)(2)(Tipp)Al=Te. This species reacts with three equivalents of CO2 across two Al-C-NHC and the Al=Te bond affording a pentacoordinate aluminum complex containing a dianionic tellurocarbonate ligand [CO2Te](2-), which is the first example of tellurium analogue of a carbonate [CO3](2-).

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2023)

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Article Chemistry, Multidisciplinary

Cooperative Activation of CO2 and Epoxide by a Heterobinuclear Al-Fe Complex via Radical Pair Mechanisms

Soumen Sinhababu et al.

Summary: This study reveals a method to activate CO2 and other substrates through cooperative behavior of two radical intermediates. The mechanistic studies show that the Al-Fe bond dissociates homolytically to generate metalloradicals, which add to the substrate in a pairwise fashion. The redox noninnocent nature of L-dipp is crucial in stabilizing the Al-II intermediates and giving them Al-III-like physical character.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2022)

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Article Chemistry, Multidisciplinary

Synthesis of Intramolecular P/Al-Based Frustrated Lewis Pairs via Aluminum-Tin-Exchange and their Reactivity toward CO2

Patrick Federmann et al.

Summary: This study focuses on Frustrated Lewis pairs (FLPs) composed of acidic alane and basic phosphane functions. The results show that CO2 can be bound to the FLPs via the C atom at the phosphane functions and the two O atoms at the Al centers. The binding strength is determined by the residues at the Al centers, and higher electronegative residues lead to higher thermodynamic stabilization and higher barriers.

CHEMISTRY-A EUROPEAN JOURNAL (2022)

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Article Chemistry, Multidisciplinary

Divergent CO2 Activation by Tuning the Lewis Acid in Iron-Based Bimetallic Systems

Helena Corona et al.

Summary: Bimetallic motifs play a crucial role in the selective activation and functionalization of CO2. This study focuses on the activation and reduction of CO2 using a concept called bimetallic frustrated Lewis pairs (FLPs). By modifying the nature of the partner Lewis acid, the researchers achieved divergent and highly chemoselective reactivity towards CO2. Experimental and computational investigations provided a rationale for the divergent reactivity and supported the heterobimetallic bonding.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2022)

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Article Chemistry, Organic

Recent Advances in Employing Catalytic Donors and Acceptors in Electron Donor-Acceptor Complex Photochemistry

Tarannum Tasnim et al.

Summary: This Synopsis highlights recent developments in electron donor-acceptor (EDA) complex photochemistry, emphasizing the importance of catalysts in this synthetic strategy.

JOURNAL OF ORGANIC CHEMISTRY (2022)

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Article Chemistry, Multidisciplinary

Taming Heavier Group 14 Imine Analogues: Accessing Tin Nitrogen [Sn=N] Double Bonds and their Cycloaddition/Metathesis Chemistry

Malte Fischer et al.

Summary: A systematic study on stable stannaimines was conducted by combining different heteroleptic stannylenes with organic azides. The reactions yielded new stannaimines with varied reactivity profiles, including activation of substrates under ambient conditions and rare examples of main group multiple bond metathesis reactions.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2022)

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Review Chemistry, Multidisciplinary

Challenges and Prospects in the Catalytic Conversion of Carbon Dioxide to Formaldehyde

Siqi Zhao et al.

Summary: This review summarizes recent progress in converting CO2 to formaldehyde using various methods and discusses the advantages and limitations of different strategies.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2022)

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Review Chemistry, Multidisciplinary

Recent Advances in Carbon Dioxide Adsorption, Activation and Hydrogenation to Methanol using Transition Metal Carbides

Prabodh Ranjan et al.

Summary: Selective hydrogenation of CO2 to methanol is a promising method to meet energy demands and rebalance the carbon cycle. Transition metal carbides (TMCs) have received considerable attention due to their excellent catalytic properties, and they play an important role in reactions such as CO2 adsorption and conversion into value-added chemicals.

CHEMSUSCHEM (2022)

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Article Chemistry, Multidisciplinary

A strained intramolecular P/Al-FLP and its reactivity toward allene

Patrick Federmann et al.

Summary: FLPs with aluminum-phosphane interactions have been synthesized using a new method, which can readily bind substrates and release strain. Additionally, this system can activate allenes for unique reactivity.

CHEMICAL COMMUNICATIONS (2022)

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Article Chemistry, Multidisciplinary

Isolating elusive 'Al(μ-O)M' intermediates in CO2 reduction by bimetallic Al-M complexes (M = Zn, Mg)

Matthew J. Evans et al.

Summary: The corresponding Al(mu-O)M complexes were isolated by the reaction of compounds containing Al-Mg and Al-Zn bonds with N2O. Electronic structure analysis revealed mainly ionic Al-O and O-M bonds in these complexes, featuring an anionic mu-oxo centre. The reaction with CO2 confirmed that these species correspond to the proposed intermediates in the formation of mu-carbonate compounds.

CHEMICAL COMMUNICATIONS (2022)

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Article Chemistry, Multidisciplinary

Carbon dioxide reduction by an Al-O-P frustrated Lewis pair

Lucas Wickemeyer et al.

Summary: The reaction between tBu(2)P(O)H and Bis(2)AlH yielded the adduct tBu(2)P(H)-O-Al(H)Bis(2). This adduct is capable of binding molecular hydrogen and forming a 1,2-adduct with CO2. Furthermore, the H-2 adduct can reduce CO2 and form a formic acid adduct.

CHEMICAL SCIENCE (2022)

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Article Chemistry, Multidisciplinary

Carbon-chalcogen bond formation initiated by [Al(NONDipp)(E)]- anions containing Al-E{16} (E{16} = S, Se) multiple bonds

Matthew J. Evans et al.

Summary: This study investigates a series of multiply-bonded main group metal compounds and their reactions with various substrates, revealing their reaction mechanisms and product structures.

CHEMICAL SCIENCE (2022)

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Review Chemistry, Inorganic & Nuclear

Recent advances in cooperative activation of CO2 and N2O by bimetallic coordination complexes or binuclear reaction pathways

Soumen Sinhababu et al.

Summary: The gaseous small molecules, CO2 and N2O, play important roles in climate change and ozone layer depletion. This perspective reviews recent advances in the cooperative activation of CO2 and N2O, which are challenging due to their inertness.

DALTON TRANSACTIONS (2022)

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Review Chemistry, Multidisciplinary

Carbon Dioxide Reduction: A Bioinspired Catalysis Approach

Yun Li et al.

Summary: Bioinspired catalysis has been recently explored for CO2 reduction, drawing from our understanding of active site structures and mechanisms to design original molecular catalysts mimicking fascinating metalloenzymes. This multidisciplinary research involves biochemical, functional, and structural characterization of enzymes, along with synthetic chemistry studies, aiming to develop highly active catalysts for the energetic transition.

ACCOUNTS OF CHEMICAL RESEARCH (2021)

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Review Chemistry, Inorganic & Nuclear

Synergy between metals for small molecule activation: Enzymes and bio-inspired complexes

Ashta C. Ghosh et al.

Summary: Transition metal-driven small molecule activation is essential for the production of fuels and chemicals or energy supply. The use of multimetallic catalysts, where two or more metal centers act in synergy to activate and transform the substrate(s), is widespread both in nature (metalloenzymes) and (bio)inorganic chemistry. Benefits of this strategy in terms of catalytic performances result from cooperation between different metals to bind and activate a single substrate, to activate different substrates reacting together, or with one assisting metal tuning the reactivity of the active metal center.

COORDINATION CHEMISTRY REVIEWS (2021)

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Article Chemistry, Multidisciplinary

Ambiphilic Al-Cu Bonding

Han-Ying Liu et al.

Summary: The reactivity of copper-alumanyl complexes is dependent on the identity of the carbene co-ligand, suggesting an ambiphilicity in the Cu-Al interaction. This divergent reactivity with carbodiimides and CO2 implies a complex relationship between the two metals in the complex.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

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Review Chemistry, Organic

Synthetic reactions driven by electron-donor-acceptor (EDA) complexes

Zhonglie Yang et al.

Summary: The electron-donor-acceptor (EDA) complex, formed by dipole-dipole interactions between an electron donor and an electron acceptor, can be transformed into the excited state upon light irradiation, leading to electron transfer and subsequent reactions. Reactions involving EDA complexes are typically mild and do not require transition metal catalysts or photosensitizers, aligning with the principles of green chemistry.

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY (2021)

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Review Chemistry, Multidisciplinary

Donor-Acceptor Type Covalent Organic Frameworks

Jinwei Zhao et al.

Summary: Covalent organic frameworks (COFs) with segregated donor-acceptor stacks provide pathways and channels for effective charge carrier transport. Significant progress has been made in the research of D-A COFs over the past decade, focusing on design principles, growing structural diversities, and promising application potentials.

CHEMISTRY-A EUROPEAN JOURNAL (2021)

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Article Chemistry, Inorganic & Nuclear

Synthesis and Reactivity of Acyclic Germanimines: Silyl Rearrangement and Cycloadditions

Matthew J. Evans et al.

Summary: This study reports the synthesis and reactivity of aromatic germanimines, demonstrating their decomposition and intramolecular reactions at different temperatures. Furthermore, it shows that these germanimines can react with various unsaturated polar substrates via a [2 + 2] cycloaddition pathway.

INORGANIC CHEMISTRY (2021)

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Article Chemistry, Multidisciplinary

Strongly Polarized Iridiumδ--Aluminumδ+ Pairs: Unconventional Reactivity Patterns Including CO2 Cooperative Reductive Cleavage

Leon Escomel et al.

Summary: The study demonstrates the formation of unusual iridium aluminum species through a reductive elimination route, showing strong polarized Al(III)-Ir(III) interactions. Reactivity studies further reveal that Lewis base binding to Al does not affect the reactivity of the Ir-Al motif, promoting cooperative reductive cleavage of various compounds.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2021)

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Article Chemistry, Multidisciplinary

Colorimetric Metal-Free Detection of Carbon Monoxide: Reversible CO Uptake by a BNB Frustrated Lewis Pair

Xiongfei Zheng et al.

Summary: Two BNB-type frustrated Lewis pairs with different B-bound fluoroaryl groups are capable of capturing gaseous CO reversibly at/above room temperature, with migration of an aryl substituent to the electrophilic carbon of the CO guest. This reversibility allows for release of captured carbon monoxide in the temperature range 40-70 degrees C, enabling potential CO sensing based on color changes.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

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Article Chemistry, Multidisciplinary

Reversible and Irreversible [2+2] Cycloaddition Reactions of Heteroallenes to a Gallaphosphene

Mahendra K. Sharma et al.

Summary: The study involved cycloaddition reactions of gallaphosphene with carbodiimides and isocyanates to synthesize four-membered and six-membered metallaheterocycles, with reversible reactions confirmed. Characterization of the compounds was carried out using IR and heteronuclear NMR spectroscopy, along with elemental analysis, while quantum chemical calculations provided insights into the energetics of the reactions.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

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Article Chemistry, Multidisciplinary

Probing the Extremes of Covalency in M-Al bonds: Lithium and Zinc Aluminyl Compounds

Matthew M. D. Roy et al.

Summary: Synthetic routes to lithium, magnesium, and zinc aluminyl complexes were reported, with the first structural characterization of an unsupported lithium-aluminium bond. Crystallographic and quantum-chemical studies revealed a highly polar Li-Al interaction with a low bond order and relatively little charge transfer from Al to Li. Comparison with magnesium and zinc aluminyl systems showed changes to both the M-Al bond and the (NON)Al fragment, indicating a more covalent character in the latter complex, which was shown to react with CO2 via a pathway where the zinc centre acts as the nucleophilic partner.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

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Article Chemistry, Multidisciplinary

Low-Valent Germanylidene Anions: Efficient Single-Site Nucleophiles for Activation of Small Molecules

Chris Gendy et al.

Summary: Rare mononuclear and helical chain low-valent germanylidene anions, synthesized by stepwise reduction from corresponding germylene precursors, exhibit electronic structures describable with ylidene and ylidone resonance forms, and act as efficient single-site nucleophiles for activating small molecules.

CHEMISTRY-A EUROPEAN JOURNAL (2021)

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Article Chemistry, Multidisciplinary

Coinage metal aluminyl complexes: probing regiochemistry and mechanism in the insertion and reduction of carbon dioxide

Caitilin McManus et al.

Summary: The synthesis of coinage metal aluminyl complexes via a salt metathesis approach allows the insertion of heteroallenes and formation of M(CE2)Al bridging units, with differences in crystal structure and reactivity observed for copper, silver, and gold. The mechanism of CO2 to CO/carbonate transformation involves extrusion of CO from M(CO)(2)Al fragment to form a bimetallic oxide that assimilates a second molecule of CO2, with energetic barriers consistent with experimental observations and trends in M-C and M-O bond strengths.

CHEMICAL SCIENCE (2021)

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Article Chemistry, Multidisciplinary

Double insertion of CO2 into an Al-Te multiple bond

Matthew J. Evans et al.

Summary: This study reports a novel ligand containing a terminal aluminium telluride bond, with DFT calculations confirming significant metal-tellurium multiple bond character. The reaction with CO2 proceeds via a double insertion to form the previously unknown tellurodicarbonate ligand.

CHEMICAL COMMUNICATIONS (2021)

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Effective and Reversible Carbon Dioxide Insertion into Cerium Pyrazolates

Uwe Bayer et al.

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Z-Scheme Photocatalytic Systems for Carbon Dioxide Reduction: Where Are We Now?

Wenhao Zhang et al.

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Radical Chemistry and Reaction Mechanisms of Propane Oxidative Dehydrogenation over Hexagonal Boron Nitride Catalysts

Xuanyu Zhang et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

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Michael L. Tarlton et al.

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Philipp Holtkamp et al.

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Douglas W. Stephan

CHEM (2020)

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Bioinspired Nickel Complexes Supported by an Iron Metalloligand

Jacob R. Prat et al.

INORGANIC CHEMISTRY (2020)

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Carbonyl group and carbon dioxide activation by rare-earth-metal complexes

Uwe Bayer et al.

DALTON TRANSACTIONS (2020)

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Addition reactions and diazomethane capture by the intramolecular P-O-B FLP: tBu2POBcat

Diya Zhu et al.

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A Neutral Geminal Tin/Phosphorus Frustrated Lewis Pair

Philipp Holtkamp et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019)

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Understanding the Individual and Combined Effects of Solvent and Lewis Acid on CO2 Insertion into a Metal Hydride

Jessica E. Heimann et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2019)

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A nucleophilic gold complex

Jamie Hicks et al.

NATURE CHEMISTRY (2019)

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Controlling Selectivity in the Hydroboration of Carbon Dioxide to the Formic Acid, Formaldehyde, and Methanol Oxidation Levels

Matthew R. Espinosa et al.

ACS CATALYSIS (2019)

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Transition-Metal-Catalyzed Carboxylation Reactions with Carbon Dioxide

Andreu Tortajada et al.

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Heterobimetallic [NiFe] Complexes Containing Mixed CO/CN- Ligands: Analogs of the Active Site of the [NiFe] Hydrogenases

Carlo U. Perotto et al.

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Nathaniel J. Hartmann et al.

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Lewis Acid Enhancement of Proton Induced CO2 Cleavage: Bond Weakening and Ligand Residence Time Effects

Joshua A. Buss et al.

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Zhongbao Jian et al.

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A Bimetallic Nickel-Gallium Complex Catalyzes CO2 Hydrogenation via the Intermediacy of an Anionic d10 Nickel Hydride

Ryan C. Cammarota et al.

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Synthesis, Structure, and Catalysis of Palladium Complexes Bearing a Group 13 Metalloligand: Remarkable Effect of an Aluminum-Metalloligand in Hydrosilylation of CO2

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Testing the Push-Pull Hypothesis: Lewis Acid Augmented N2 Activation at Iron

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Group6 Transition-Metal/Boron Frustrated Lewis Pair Templates Activate N2 and Allow its Facile Borylation and Silylation

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Frustrated Lewis Pair Chemistry: Searching for New Reactions

Gerald Kehr et al.

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Helmut Schwarz

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Design principles in frustrated Lewis pair catalysis for the functionalization of carbon dioxide and heterocycles

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Selective reduction of carbon dioxide to bis(silyl)acetal catalyzed by a PBP-supported nickel complex

Pablo Rios et al.

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Sebastien Bontemps

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Transition metal mediated coupling of carbon dioxide and ethene to acrylic acid/acrylates

Manuela Hollering et al.

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Interrogating heterobimetallic co-catalytic responses for the electrocatalytic reduction of CO2 using supramolecular assembly

Charles W. Machan et al.

DALTON TRANSACTIONS (2016)

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Small Molecule Activation by Intermolecular Zr(IV)-Phosphine Frustrated Lewis Pairs

Owen J. Metters et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2016)

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A Significant but Constrained Geometry Pt→Al Interaction: Fixation of CO2 and CS2, Activation of H2 and PhCONH2

Marc Devillard et al.

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Manganese Electrocatalysts with Bulky Bipyridine Ligands: Utilizing Lewis Acids To Promote Carbon Dioxide Reduction at Low Overpotentials

Matthew D. Sampson et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2016)

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Implications of CO2 Activation by Frustrated Lewis Pairs in the Catalytic Hydroboration of CO2: A View Using N/Si+ Frustrated Lewis Pairs

N. von Wolff et al.

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Encapsulating Inorganic Acetylene, HBNH, Using Flanking Coordinative Interactions

Anindya K. Swarnakar et al.

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Frustrated Lewis Pair Chemistry: Development and Perspectives

Douglas W. Stephan et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2015)

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Activation of Carbon Dioxide by Silyl Triflate-Based Frustrated Lewis Pairs

Sarah A. Weicker et al.

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Reductive functionalization of CO2 with amines: an entry to formamide, formamidine and methylamine derivatives

Anis Tlili et al.

GREEN CHEMISTRY (2015)

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Frustrated Lewis Pairs

Douglas W. Stephan

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2015)

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Facile Reversibility by Design: Tuning Small Molecule Capture and Activation by Single Component Frustrated Lewis Pairs

Zhenbo Mo et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2015)

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Catalyst Control of Selectivity in CO2 Reduction Using a Tunable Heterobimetallic Effect

Sharareh Bagherzadeh et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2015)

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Iron-Catalyzed Reduction of CO2 into Methylene: Formation of C-N, C-O, and C-C Bonds

Guanghua Jin et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2015)

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Using carbon dioxide as a building block in organic synthesis

Qiang Liu et al.

NATURE COMMUNICATIONS (2015)

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Cooperative Lewis Pairs Based on Late Transition Metals: Activation of Small Molecules by Platinum(0) and B(C6F5)3

Sebastian J. K. Forrest et al.

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Upgrading Carbon Dioxide by Incorporation into Heterocycles

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Formation of a nickel carbon dioxide adduct and its transformation mediated by a Lewis acid

Yeong-Eun Kim et al.

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Metal-Free Reduction of CO2 with Hydroboranes: Two Efficient Pathways at Play for the Reduction of CO2 to Methanol

Christophe Das Neves Gomes et al.

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Application of the Donor-Acceptor Concept to Intercept Low Oxidation State Group 14 Element Hydrides using a Wittig Reagent as a Lewis Base

Anindya K. Swarnakar et al.

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Review Biotechnology & Applied Microbiology

Use of carbon dioxide as feedstock for chemicals and fuels: homogeneous and heterogeneous catalysis

Angela Dibenedetto et al.

JOURNAL OF CHEMICAL TECHNOLOGY AND BIOTECHNOLOGY (2014)

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Multimetallic Cooperativity in Uranium-Mediated CO2 Activation

Oliver Cooper et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2014)

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Frustrated Lewis pair chemistry of carbon, nitrogen and sulfur oxides

Douglas W. Stephan et al.

CHEMICAL SCIENCE (2014)

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Trapping Formaldehyde in the Homogeneous Catalytic Reduction of Carbon Dioxide

Sebastien Bontemps et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2013)

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Review Chemistry, Multidisciplinary

Frontiers, Opportunities, and Challenges in Biochemical and Chemical Catalysis of CO2 Fixation

Aaron M. Appel et al.

CHEMICAL REVIEWS (2013)

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Article Chemistry, Inorganic & Nuclear

Synthesis, Structure, and Reactivity of an Anionic Zr-Oxo Relevant to CO2 Reduction by a Zr/Co Heterobimetallic Complex

Jeremy P. Krogman et al.

INORGANIC CHEMISTRY (2013)

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