Development of a General and Selective Nanostructured Cobalt Catalyst for the Hydrogenation of Benzofurans, Indoles and Benzothiophenes

Angewandte Chemie International Edition, Год журнала: 2023, Номер 62(10)

Опубликована: Янв. 13, 2023

The selective hydrogenation of benzofurans in the presence a heterogeneous non-noble metal catalyst is reported. developed optimal catalytic material consists cobalt-cobalt oxide core-shell nanoparticles supported on silica, which has been prepared by immobilization and pyrolysis cobalt-DABCO-citric acid complex silica under argon at 800 °C. This novel allows for simple functionalized to 2,3-dihydrobenzofurans as well related heterocycles. versatility reported protocol showcased reduction selected drugs deuteration Further, stability, recycling, reusability Co-nanocatalyst are demonstrated.

Язык: Английский

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Ru-NHC-Catalyzed Asymmetric, Complete Hydrogenation of Indoles and Benzofurans: One Catalyst with Dual Function

Journal of the American Chemical Society, Год журнала: 2023, Номер 145(29), С. 15695 - 15701

Опубликована: Июль 12, 2023

The highly enantioselective and complete hydrogenation of protected indoles benzofurans has been developed, affording facile access to a range chiral three-dimensional octahydroindoles octahydrobenzofurans, which are prevalent in many bioactive molecules organocatalysts. Remarkably, we control the nature ruthenium N-heterocyclic carbene complex employed as both homogeneous heterogeneous catalysts, providing new avenues for its potential applications asymmetric more challenging aromatic compounds.

Язык: Английский

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Enantioselective Phase-Transfer-Catalyzed Synthesis of Spirocyclic Azetidine Oxindoles

Organic Letters, Год журнала: 2024, Номер 26(10), С. 2079 - 2084

Опубликована: Март 6, 2024

Spiro-3,2′-azetidine oxindoles combine two independently important pharmacophores in an understudied spirocyclic motif that is attractive for medicinal chemistry. Here, the enantioselective synthesis of these structures achieved up to 2:98 er through intramolecular C–C bond formation, involving activation substrate with a novel SF5-containing chiral cation phase-transfer (PT) catalyst. The products are readily elaborated/deprotected afford medicinally relevant enantioenriched compounds. Control experiments suggest interfacial PT mechanism, whereby catalytic asymmetric induction chloride leaving group.

Язык: Английский

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Asymmetric Full Saturation of Vinylarenes with Cooperative Homogeneous and Heterogeneous Rhodium Catalysis

Journal of the American Chemical Society, Год журнала: 2021, Номер 143(48), С. 20377 - 20383

Опубликована: Ноя. 22, 2021

Homogeneous and heterogeneous catalyzed reactions can seldom operate synergistically under the same conditions. Here we communicate use of a single rhodium precursor that acts in both homogeneous phases for asymmetric full saturation vinylarenes that, to date, constitute an unmet bottleneck field. A simple hydrogenation styrenic olefin, enabled by ligand accelerated effect, accounted facial selectivity consecutive arene hydrogenation. Tuning ratio between phosphine controlled formation catalytic species without interference from each other. The system is flexible terms chiral nature external olefin. We anticipate our findings will promote development hydrogenations.

Язык: Английский

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Rh-Catalyzed Sequential Asymmetric Hydrogenations of 3-Amino-4-Chromones Via an Unusual Dynamic Kinetic Resolution Process

Journal of the American Chemical Society, Год журнала: 2022, Номер 144(43), С. 20078 - 20089

Опубликована: Окт. 18, 2022

Rh-catalyzed sequential asymmetric hydrogenations of 3-amino-4-chromones have been achieved for the first time via an unprecedented dynamic kinetic resolution under neutral conditions, providing (S,R)-3-amino-4-chromanols in high yields (up to 98%) with excellent enantio- and diastereoselectivities 99.9% ee 20:1 dr). The mechanistic studies based on control experiments density functional theory (DFT) calculations suggest that process intermediate enantiomers generated hydrogenation step proceeded a stereomutation (or called chiral assimilation) pathway from undesired enantiomer desired rather than traditional racemization enantiomer. protocol can be performed gram scale relatively low catalyst loading offers practical convenient synthesizing series bioactive chromanols their derivatives.

Язык: Английский

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Rhodium‐Catalyzed Asymmetric Hydrogenation of 3‐Benzoylaminocoumarins for the Synthesis of Chiral 3‐Amino Dihydrocoumarins

Angewandte Chemie International Edition, Год журнала: 2021, Номер 60(44), С. 23602 - 23607

Опубликована: Окт. 1, 2021

An asymmetric hydrogenation of 3-benzoylaminocoumarins was achieved for the first time using our BridgePhos-Rh catalytic system, providing chiral 3-amino dihydrocoumarins in high yields (up to 98 %) and with excellent enantioselectivities 99.7 % ee). The relationship between hydrogenations dihedral angles resulting π-π stacking effects complexes, which were determined by X-ray diffraction analysis, are discussed. corresponding hydrogenated products allow many transformations, several skeletons important physiological pharmacological activities.

Язык: Английский

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Catalyst- and Oxidizing Reagent-Free Electrochemical Benzylic C(sp³)–H Oxidation of Phenol Derivatives

The Journal of Organic Chemistry, Год журнала: 2022, Номер 87(12), С. 7806 - 7817

Опубликована: Июнь 1, 2022

A site-selective electrochemical approach for the benzylic C(sp3)-H oxidation reaction of phenol derivatives along with hydrogen evolution has been developed. The protocol proceeds in an easily available undivided cell at room temperature under catalyst- and oxidizing reagent-free conditions. corresponding aryl aldehydes ketones are obtained satisfactory yields, gram-scale synthesis is easy to be carried out.

Язык: Английский

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Rhodium‐Catalyzed Asymmetric Hydrogenation of All‐Carbon Aromatic Rings

Angewandte Chemie International Edition, Год журнала: 2022, Номер 61(34)

Опубликована: Июнь 29, 2022

Compared with heteroarenes, homogeneous asymmetric hydrogenation of all-carbon aromatic rings is a longstanding challenge in organic synthesis due to the strong aromaticity and difficult enantioselective control. Herein, we report rhodium/diphosphine-catalyzed rings, affording series axially chiral cyclic compounds high enantioselectivity through desymmetrization or kinetic resolution. In addition, central-chiral were also obtained by phenanthrenes bearing directing group. The key success introduction diphosphine ligands steric hindrance electron-donating properties. monophosphine could be simple conversion products phosphine atom.

Язык: Английский

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Improving reproducibility through condition-based sensitivity assessments: application, advancement and prospect

Chemical Science, Год журнала: 2024, Номер 15(36), С. 14548 - 14555

Опубликована: Янв. 1, 2024

The fluctuating reproducibility of scientific reports presents a well-recognised issue, frequently stemming from insufficient standardisation, transparency and lack information in publications.

Язык: Английский

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Dearomative selective reduction of structurally diverse N-heteroarenes enabled by a homogeneous titanium catalyst

Journal of Catalysis, Год журнала: 2025, Номер unknown, С. 115937 - 115937

Опубликована: Янв. 1, 2025

Язык: Английский

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