Molybdenum-doped carbon nitride as an efficient heterogeneous catalyst for direct amination of nitroarenes with arylboronic acids

Chinese Chemical Letters, Год журнала: 2024, Номер unknown, С. 110001 - 110001

Опубликована: Май 1, 2024

Язык: Английский

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Porous carbon catalysis in sustainable synthesis of functional heterocycles: An overview

Chinese Chemical Letters, Год журнала: 2024, Номер 35(8), С. 109472 - 109472

Опубликована: Янв. 1, 2024

Язык: Английский

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Synthetic and Mechanistic Studies into the Reductive Functionalization of Nitro Compounds Catalyzed by an Iron(salen) Complex

Journal of the American Chemical Society, Год журнала: 2024, Номер 146(29), С. 19839 - 19851

Опубликована: Июль 12, 2024

We report on the use of a simple, bench-stable [Fe(salen)2]-μ-oxo precatalyst in reduction nitro compounds. The reaction proceeds at room temperature across range substrates, including aromatics and aliphatics. By changing reducing agent from pinacol borane (HBpin) to phenyl silane (H3SiPh), we can chemoselectively reduce compounds while retaining carbonyl functionality. Our mechanistic studies, which include kinetics, electron paramagnetic resonance (EPR), mass spectrometry, quantum chemistry, indicate presence nitroso intermediate generation an on-cycle iron hydride as key catalytic intermediate. Based this insight, were able extend chemistry hydroamination identified simple substrate feature (alkene lowest unoccupied molecular orbital (LUMO) energy) that could be used predict alkenes would result productive catalysis.

Язык: Английский

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Selectivity Effects of Hydrogen Acceptors and Catalyst Structures in Alcohol Oxidations Using (Cyclopentadienone)iron Tricarbonyl Compounds

The Journal of Organic Chemistry, Год журнала: 2025, Номер 90(5), С. 2036 - 2051

Опубликована: Янв. 23, 2025

Oppenauer-type oxidations are catalyzed by air- and moisture-stable, sustainable, (cyclopentadienone)iron carbonyl compounds, but the substrate scope is limited due to low reduction potential of acetone, which most commonly used hydrogen acceptor. We discovered that furfural, an aldehyde derived from cellulosic biomass, effective acceptor with this class catalysts. In general, reactions using furfural as led higher isolated yields ketones aldehydes compared those acetone. Importantly, primary benzylic allylic alcohols─typically a challenging alcohols oxidize these catalysts─could be oxidized. The selectivity for vs secondary alcohol oxidation catalysts was also explored acetone acceptors. Most tested preferentially oxidized unhindered alcohols, trialkylsilyl groups in 2- 5-positions cyclopentadienone alcohols. A combination experiments kinetic studies concluded trialkylsilyl-based kinetically derived─primary were more quickly than secondary─and other arose equilibrium-driven nature oxidation.

Язык: Английский

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Rh(III)‐Catalyzed Direct ortho Alkylation of Carbazoles with Nitroalkenes

Advanced Synthesis & Catalysis, Год журнала: 2023, Номер 365(20), С. 3461 - 3466

Опубликована: Авг. 26, 2023

Abstract The Rh(III)‐catalyzed ortho alkylation of N ‐pyridylcarbazoles with nitroalkenes has been developed, furnishing a wide range 2‐(2‐nitroalkyl)carbazoles. Both aromatic and aliphatic participated in this reaction successfully. This protocol also proceeded well an indoline based substrate. Derivatization the representative nitroalkane product was described.

Язык: Английский

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Photo-driven reduction/cyclization of nitroarenes via electron donor-acceptor complexes: a novel acquisition for N-heterocycles

Green Chemistry, Год журнала: 2024, Номер 26(23), С. 11531 - 11539

Опубликована: Янв. 1, 2024

An EDA complex-based method for the reduction/cyclization of nitroarenes to obtain N -heterocycles with H 2 O as a clean by-product is presented.

Язык: Английский

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Pd‐Catalyzed Decarboxylative Cross‐Coupling of N‐Aryl Anthranilic Acids to Access Carbazoles: Gram Scale Total Synthesis of Anti‐ Cancer Drug Ellipticine

Asian Journal of Organic Chemistry, Год журнала: 2023, Номер 12(11)

Опубликована: Авг. 18, 2023

Abstract An efficient and scalable Pd‐catalyzed decarboxylative cross‐coupling strategy for the synthesis of carbazoles has been developed by using N‐aryl anthranilic acids. By employing a well‐designed catalytic system, this protocol access diverse carbazole derivatives via C−C bond‐formation in one‐pot. The substituted were obtained good to excellent yields with high functional‐group tolerance. We have also demonstrated gram‐scale anti‐cancer drug Ellipticine utilizing methodology. This concise total ellipticine exemplifies efficiency our methodology producing significant compound.

Язык: Английский

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Preparation of Carbazoles Involving 6π‐Electrocyclization, Photoredox‐, Electrochemical‐, and Thermal Cyclization Reactions: Mechanistic Insights

Chemistry - A European Journal, Год журнала: 2023, Номер 30(8)

Опубликована: Ноя. 30, 2023

Carbazole is a heterocyclic motif that can be found in diverse array of natural and unnatural products displaying wide range biological physiological properties. Furthermore, this heterocycle part electronic materials like photoconducting polymers organic optoelectronic owing to its excellent photophysical characteristics. Consequently, the development synthetic strategies for carbazole scaffolds holds potential significance material fields. In regard, variety preparation methods has been developed exploit their efficient distinct formation new C-C C-heteroatom bonds under mild conditions enabling broad substrate diversity functional group tolerance. Therefore, review focuses on synthesis set derivatives describing methodologies involve direct irradiation, photosensitization, photoredox, electrochemical thermal cyclization reactions.

Язык: Английский

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Copper‐catalyzed intramolecular annulation through C–H activation: Synthesis of carbazolones

Applied Organometallic Chemistry, Год журнала: 2023, Номер 37(7)

Опубликована: Апрель 19, 2023

An efficient protocol for synthesizing carbazolones from anilines and 1,3‐diketones by copper‐catalyzed intramolecular oxidative C–C coupling through the selective activation of C–H bond is reported.

Язык: Английский

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Iron-catalyzed intramolecular reductive cyclization of o-nitroarenes to indoles under visible light irradiation

Tetrahedron Letters, Год журнала: 2023, Номер 123, С. 154543 - 154543

Опубликована: Май 16, 2023

Язык: Английский

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