Transition metal-free synthesis of 2-aryl quinazolines via alcohol dehydrogenation

Molecular Catalysis, Journal Year: 2023, Volume and Issue: 542, P. 113110 - 113110

Published: April 6, 2023

We report here a transition metal-free synthesis of quinazoline derivatives starting from 2-aminobenzyl alcohols and aryl amides via an alcohol dehydrogenation strategy promoted by potassium tertiary butoxide. The control experiments are carried out to identify the reaction intermediates role K+ ion in reaction. DFT calculations unveil mechanism, with special focus on rate determining state. present method tolerates variety functional groups providing easy access diversely substituted quinazolines.

Language: Английский

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Biogenic synthesis of δ‐MnO₂ nanoparticles: A sustainable approach for C‐alkylation and quinoline synthesis via acceptorless dehydrogenation and borrowing hydrogen reactions

Applied Organometallic Chemistry, Journal Year: 2023, Volume and Issue: 37(7)

Published: April 26, 2023

The sustainable and environmentally benign biogenic synthesis of manganese‐oxide nanoparticles (MnO 2 NPs) in a single crystalline δ ‐phase its subsequent synthetic utility have been described. synthesized ‐MnO NPs were characterized using scanning electron microscopy (SEM), energy dispersive X‐ray (EDX), diffraction (XRD) analysis techniques. detailed envisages the reduction Mn(VII) to Mn(IV) was facilitated by various phytochemicals present aq. mango leaves extract, avoiding use external ligand source. perceived delta ( ) monoclinic phase, wherein spherical agglomerated morphology displayed with particle size <5 nm. Further, newly developed showcased for alpha‐keto‐alkylation quinoline via hydrogen autotransfer acceptorless dehydrogenative coupling strategy. Moreover, series control experiments, mechanistic elucidation, catalyst recyclability, dye removal study demonstrated.

Language: Английский

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A sustainable approach for nickel nanoparticles synthesis: expeditious access to N-heterocycles under heterogeneous condition and photophysical studies

New Journal of Chemistry, Journal Year: 2023, Volume and Issue: 47(17), P. 8268 - 8276

Published: Jan. 1, 2023

A sustainable and environmentally benign biogenic technique for one-step synthesis of Ni-NPs (NiC 2 O 4 ·2H O-NPs) using Portulaca oleracea (purslane) leaf extract has been disclosed the first time.

Language: Английский

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3d Transition Metal Complexes as Homogeneous Catalysts in N-Alkylation Reactions Using Alcohols: A Recent Update

Tetrahedron, Journal Year: 2024, Volume and Issue: 165, P. 134192 - 134192

Published: Aug. 13, 2024

Language: Английский

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Fe-Catalyzed Hydrocyclization of Inactivated Alkenes to Synthesize Ring-Fused 2,3-Dihydroquinazolinone

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: 90(4), P. 1507 - 1513

Published: Jan. 22, 2025

A Fe-catalyzed hydrocyclization reaction of unactivated alkenes was developed, utilizing PhSiH3 as the hydrogen source, yielding 2,3-dihydroquinazolinone (DHQZ) derivatives in moderate to good yields. Notably, when substrate switched N-cyano-N-(2-(prop-1-en-2-yl)phenyl)benzamides, yielded only unreduced products. Mechanistic studies revealed that intramolecular addition situ formed radical alkene results formation fused ring.

Language: Английский

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CuO NPs catalyzed synthesis of quinolines, pyridines, and pyrroles via dehydrogenative coupling strategy

Journal of Catalysis, Journal Year: 2022, Volume and Issue: 413, P. 1017 - 1027

Published: Aug. 13, 2022

Language: Английский

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α-Methylation of Ketones and Indoles Catalyzed by a Manganese(I) PC_NHCP Pincer Complex with Methanol as a C₁ Source

Organometallics, Journal Year: 2022, Volume and Issue: 42(1), P. 62 - 71

Published: Dec. 28, 2022

Acceptorless alcohol dehydrogenation is a powerful reaction in sustainable synthesis. When combined tandem with dehydrogenative coupling or hydrogen borrowing, acceptorless can be used for the environmentally benign construction of C–C, C–N, and C–O bonds. While many these reactions rely on using precious metals, past decade use earth-abundant metals has become more prevalent. If green renewable feedstock could introduced as well, sustainability further increased. Methanol would such substrate serve C1 source when methylation wide variety substrates. Herein, we report efficient manganese-catalyzed α-methylation ketones indoles. The manganese catalyst based PCNHCP pincer platform containing rare central carbene donor. supports diverse set functional groups, occurs at moderate temperatures (110 °C), provides corresponding methylated indoles excellent yields. In contrast to previously reported mechanisms, herein mechanism does not depend metal–ligand cooperativity but rather proceeds via (i) metal-based featuring hydride (ii) ligand-centered where manganese-carbonyl acts catalytic center, depending additive.

Language: Английский

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Nickel‐Catalyzed Chemodivergent Coupling of Alcohols: Efficient Routes to Access α,α‐Disubstituted Ketones and α‐Substituted Chalcones

Chemistry - A European Journal, Journal Year: 2024, Volume and Issue: 30(15)

Published: Jan. 17, 2024

Abstract Chemodivergent (de)hydrogenative coupling of primary and secondary alcohols is achieved utilizing an inexpensive nickel catalyst, (6‐OH‐bpy)NiCl 2 . This protocol demonstrates the synthesis branched carbonyl compounds, α , ‐disubstituted ketones, ‐substituted chalcones via borrowing hydrogen strategy acceptorless dehydrogenative coupling, respectively. A wide range aryl‐based are coupled with various in this tandem dehydrogenation/hydrogenation reaction. The along KO t Bu or K CO 3 governed selectivity for formation saturated ketones chalcones. preliminary mechanistic investigation confirms reversible dehydrogenation to carbonyls metal‐ligand cooperation (MLC) involvement radical intermediates during

Language: Английский

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Nickel Pincer Complexes Catalyzed Sustainable Synthesis of 3,4-Dihydro-2H-1,2,4-benzothiadiazine-1,1-dioxides via Acceptorless Dehydrogenative Coupling of Primary Alcohols

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(4), P. 2494 - 2504

Published: Feb. 7, 2024

We report the atom-economic and sustainable synthesis of biologically important 3,4-dihydro-2H-1,2,4-benzothiadiazine-1,1-dioxide (DHBD) derivatives from readily available aromatic primary alcohols 2-aminobenzenesulfonamide catalyzed by nickel(II)-N∧N∧S pincer-type complexes. The synthesized nickel complexes have been well-studied elemental spectroscopic (FT-IR, NMR, HRMS) analyses. solid-state molecular structure complex 2 has authenticated a single-crystal X-ray diffraction study. Furthermore, series (24 examples) utilizing 3 mol % Ni(II) catalyst through acceptorless dehydrogenative coupling benzyl with benzenesulfonamide. Gratifyingly, catalytic protocol is highly selective yield up to 93% produces eco-friendly water/hydrogen gas as byproducts. control experiments plausible mechanistic investigations indicate that in situ generated aldehyde benzenesulfonamide leads desired product. In addition, large-scale one thiadiazine unveils synthetic usefulness current methodology.

Language: Английский

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Selective cross-coupling of α,β-unsaturated nitriles with aldehydes or alcohols by hydrogen transfer catalysis towards β-ketonitriles and glutaronitriles

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(9), P. 2613 - 2623

Published: Jan. 1, 2024

A Ru-catalyzed selective hydroacylation of acrylonitriles with aldehydes or alcohols towards β-ketonitriles is established. Glutaronitriles can be obtained through a one-step tandem and Michael addition acrylonitrile alcohols.

Language: Английский

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