Highly Atom Economical Molecular Transformation via Hetero-Nickelacycle

Ogoshi, Sensuke

doi:10.1246/bcsj.20170268

Cited by 29 publications

(10 citation statements)

References 40 publications

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“…41,42 In this case, the reduction of the o-bromoaryl nickel complex 28 with sodium amalgam furnished naphthalyne complex 29, which reacts with TFE to form nickelacycle 30. Our group has developed a variety of nickel-catalyzed transformations of unsaturated molecules via the formation of nickelacycles, 43,44 with particular focus on the characterization of possible reaction intermediates. In this context, we wanted to the possibility of a catalytic transformation of TFE with unsaturated molecules using nickel catalysts.…”

Section: Who Usedmentioning

confidence: 99%

“…Our group has developed a variety of nickel-catalyzed transformations of unsaturated molecules via the formation of nickelacycles, 43,44 with particular focus on the characterization of possible reaction intermediates. In this context, we wanted to explore the possibility of a catalytic transformation of TFE with unsaturated molecules using nickel cat-…”

Section: Scheme 11 Catalytic Coupling Of Two Molecules Of Tfe With Hmentioning

confidence: 99%

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Transformation of Tetrafluoroethylene Using Transition-Metal Complexes

Doi¹,

Zhou²,

Ogoshi³

2022

Synthesis

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Tetrafluoroethylene (TFE) is an industrial organofluorine feedstock that is used predominantly to fabricate fluorinated polymers. TFE exhibits excellent potential as a building block for synthesizing organofluorine compounds, which are increasingly gaining attention as functional materials, pharmaceuticals, and agrochemicals. In particular, the use of transition-metal complexes in the transformation of TFE is of great interest, considering their widespread use in syntheses of organofluorine compounds over the last decades. This review highlights studies on the transformation of TFE into organofluorine compounds using transition-metal complexes, except for polymerizations. Our review covers cross-coupling reactions via C−F bond cleavage, fluoroalkylation reactions, multi-component couplings, and olefin metathesis. 1. Introduction 2. Palladium complexes 3. Copper complexes 4. Nickel complexes 5. Ruthenium complexes 6. Rhodium complexes 7. Summary and perspective

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Section: Who Usedmentioning

confidence: 99%

Section: Scheme 11 Catalytic Coupling Of Two Molecules Of Tfe With Hmentioning

confidence: 99%

Transformation of Tetrafluoroethylene Using Transition-Metal Complexes

Doi¹,

Zhou²,

Ogoshi³

2022

Synthesis

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“…Multicomponent reactions (MCRs) involve three or more substrates in a single step. MCRs are atom-economical and step-economical and hence are useful tools for synthesizing dyes, functional polymers, and physiologically active compounds. − The Povarov reaction is a representative MCR that affords quinoline derivatives from anilines, aldehydes, and dienophiles such as electron-rich alkenes and alkynes. − Scheme a shows an example of the Povarov reaction used for the synthesis of aryl-substituted quinolines. Imine formation, followed by aza-Diels–Alder reaction with alkynes, affords a dihydroquinoline; a subsequent oxidation reaction gives the corresponding aryl-substituted quinolone derivative.…”

Section: Introductionmentioning

confidence: 99%

One-Pot Synthesis of Triazatriphenylene Using the Povarov Reaction

et al. 2021

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The Povarov reaction combines aromatic amines, aldehydes, and alkynes in a single step and is regarded as an annulative π-extension reaction of aromatic amines. In this study, the Povarov reaction was investigated as an efficient tool for the synthesis of aza-polycyclic aromatic hydrocarbons via multiple π-extensions. The double Povarov reaction of 1,4-diaminobenzene yielded the 4,7phenanthroline derivative as the major product, regardless of the steric repulsion in the product. The site selectivity mainly depended on the HOMO distribution of the intermediate rather than the steric factor. Based on these insights, a 1,5,9-triazatriphenylene derivative was synthesized via a triple Povarov reaction. The structures of the synthesized compounds were unambiguously determined by single-crystal X-ray diffraction analysis. The triazatriphenylene derivative formed a smooth and stable thin film upon vacuum vapor deposition and served as a hole-blocking material in organic light-emitting diodes.

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“…Our research group has been focusing on the transformation of TFE by oxidative cyclization with Ni(0) as the key reaction step. − Such oxidative cyclization can efficiently produce a nickelacycle under concomitant formation of a C–C bond from various combinations of two π-components, where the generated nickelacycle serves as the key intermediate in such multicomponent coupling reactions . Very recently, we have disclosed a Ni-catalyzed three-component coupling reaction of TFE and aldehydes with silanes via oxa-nickelacycle key intermediates .…”

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Ni(0)-Catalyzed Three-Component Coupling Reaction of Tetrafluoroethylene and N-Sulfonyl-Substituted Imines with Silanes via Aza-Nickelacycles

2018

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A nickel-catalyzed three-component coupling reaction of tetrafluoroethylene (TFE) and N-sulfonyl-substituted imines with silanes that furnishes a variety of fluorine-containing amines is disclosed. Stoichiometric experiments revealed that the aza-nickelacycles generated upon oxidative cyclization of TFE and N-sulfonyl-substituted imines on Ni(0) were identified as the key intermediates in this catalytic reaction. A single-crystal X-ray diffraction analysis of such an aza-nickelacycle revealed that the O atom of the N-sulfonyl group stabilizes the key intermediate via coordination to the nickel center.

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Highly Atom Economical Molecular Transformation via Hetero-Nickelacycle

Cited by 29 publications

References 40 publications

Transformation of Tetrafluoroethylene Using Transition-Metal Complexes

Transformation of Tetrafluoroethylene Using Transition-Metal Complexes

One-Pot Synthesis of Triazatriphenylene Using the Povarov Reaction

Ni(0)-Catalyzed Three-Component Coupling Reaction of Tetrafluoroethylene and N-Sulfonyl-Substituted Imines with Silanes via Aza-Nickelacycles

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