Pyrazolyl-pyrimidine porous-organic-polymer supported single-site nickel composites as efficient catalysts for the synthesis of substituted pyrimidines

Chemical Engineering Journal, Journal Year: 2023, Volume and Issue: 474, P. 145642 - 145642

Published: Aug. 25, 2023

Language: Английский

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Electrochemical deposition for metal organic Frameworks: Advanced Energy, Catalysis, sensing and separation applications

Journal of Electroanalytical Chemistry, Journal Year: 2023, Volume and Issue: 937, P. 117417 - 117417

Published: April 5, 2023

Language: Английский

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N-Alkylation of Amines by C1–C10 Aliphatic Alcohols Using A Well-Defined Ru(II)-Catalyst. A Metal–Ligand Cooperative Approach

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(9), P. 5944 - 5961

Published: April 13, 2023

A Ru(II)-catalyzed efficient and selective N-alkylation of amines by C1-C10 aliphatic alcohols is reported. The catalyst [Ru(L1a)(PPh3)Cl2] (1a) bearing a tridentate redox-active azo-aromatic pincer, 2-((4-chlorophenyl)diazenyl)-1,10-phenanthroline (L1a) air-stable, easy to prepare, showed wide functional group tolerance requiring only 1.0 mol % (for N-methylation N-ethylation) 0.1 loading for with C3-C10 alcohols. array N-methylated, N-ethylated, N-alkylated were prepared in moderate good yields via direct coupling 1a efficiently catalyzes the diamines selectively. It even suitable synthesizing using (aliphatic) diols producing tumor-active drug molecule MSX-122 yield. excellent chemo-selectivity during oleyl alcohol monoterpenoid β-citronellol. Control experiments mechanistic investigations revealed that 1a-catalyzed reactions proceed borrowing hydrogen transfer pathway where removed from dehydrogenation step stored ligand backbone 1a, which subsequent steps transferred situ formed imine intermediate produce amines.

Language: Английский

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Zn(II)-Catalyzed Multicomponent Sustainable Synthesis of Pyridines in Air

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(6), P. 3650 - 3665

Published: Feb. 28, 2023

Herein, we report a Zn(II)-catalyzed solvent-free sustainable synthesis of tri- and tetra-substituted pyridines using alcohols as the primary feedstock NH4OAc nitrogen source. Using well-defined air-stable Zn(II)-catalyst, 1a, featuring redox-active tridentate azo-aromatic pincer, 2-((4-chlorophenyl)diazenyl)-1,10-phenanthroline (La), wide variety unsymmetrical 2,4,6-substituted were prepared by three-component coupling secondary with NH4OAc. Catalyst 1a is equally compatible four-component coupling. Unsymmetrical also via alcohol two different A series up to 67% yield 1-phenylpropan-1-one or 1,2-diphenylethan-1-one The 1a-catalyzed reactions proceeded efficiently upon replacing corresponding ketones, producing desired in higher yields shorter reaction time. few control experiments performed unveil mechanistic aspects, which indicates that active participation aryl-azo ligand during catalysis enables Zn(II)-complex act an efficient catalyst for present multicomponent reactions. Aerial oxygen acts oxidant dehydrogenation alcohols, H2O H2O2 byproducts.

Language: Английский

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Zn(II)‐Stabilized Azo‐Anion Radical Catalyzed Sustainable C−C Bond Formation: Regioselective Alkylation of Fluorene, Oxindole, and Indoles

ChemCatChem, Journal Year: 2024, Volume and Issue: 16(10)

Published: Feb. 7, 2024

Abstract Herein we report a sustainable approach for the alkylation of ketones, 9 H ‐fluorene, oxindole, and indole using alcohols as alkylating agent catalyzed by well‐defined air‐stable zinc catalyst ( 1 ) tridentate redox non‐innocent arylazo ligand, 2‐((4‐chlorophenyl)diazenyl)‐1,10‐phenanthroline L ). 2–3 mol % efficiently produces substituted α‐alkylated 9‐alkylated fluorenes, C3 ‐alkylated oxindoles, indoles in moderate to good isolated yields. In aerial condition, formation bis(indolyl)methane (BIMs) derivatives were observed when subjected primary alcohols. A few drug molecules containing BIMs prepared The exhibited chemoselectivity during functionalization fluorene with oleyl alcohol β‐citronellol. control experiments, including deuterium labeling performed unveil reaction mechanism indicate that one‐electron reduced azo‐anion radical species [ ]‐formed situ, acts active catalyst. All events occur at redox‐active aryl‐azo which reservoir hydrogen electrons throughout catalytic cycle, keeping Zn(II)‐center template.

Language: Английский

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Transition-Metal Catalyzed Synthesis of Pyrimidines: Recent Advances, Mechanism, Scope and Future Perspectives

Topics in Current Chemistry, Journal Year: 2024, Volume and Issue: 382(1)

Published: Jan. 31, 2024

Language: Английский

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Coordinatively fluxional diazo-based organo-electrocatalyst for conversion of CO2 to C2 and C3 products

Materials Today Catalysis, Journal Year: 2024, Volume and Issue: 5, P. 100049 - 100049

Published: March 11, 2024

The conversion of carbon dioxide (CO2) into valuable chemicals, specifically C2 and C3, through metal-free electrocatalysis remains a formidable challenge. Breaking away from traditional transition metal complexes, the focus is on designing selecting efficient organic catalysts. In this pursuit, diazo-based bulky ligand emerges as promising candidate, offering solution that both sustainable renewable. key feature its low-lying π* (LUMO), enabling it to readily accept an electron in electrochemical environment when potential applied. synthesized Diazo-based ligands have been meticulously characterized using various techniques, including 1H NMR, 13C UV-Vis, IR spectroscopy. This serves electrocatalyst, undergoing reduction triplet diradical acts nucleophile. aqueous medium, forms adduct with CO2, leading generation formyl radical. radical further couples produce acetic acid acetone efficiencies 19.6% 24.2%, respectively, at pH 5.5. To provide deeper understanding, we present proposed mechanism pathway supported by in-situ UV-Vis spectroscopy comprehensive Density Functional Theory (DFT) study. These findings mark significant step forward field electrocatalysis, approach CO2 contributing development renewable environmentally friendly systems.

Language: Английский

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Monoacetylated bishydroperoxide-derived singlet molecular oxygen-mediated oxidative coupling of primary and secondary alcohols with phenylhydrazine: Synthesis of 1,3,5-trisubstituted pyrazoles

Journal of Chemical Sciences, Journal Year: 2025, Volume and Issue: 137(1)

Published: Feb. 27, 2025

Language: Английский

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Copper(I) hydrazonate complexes as efficient catalysts for synthesizing substituted pyrimidines via acceptorless dehydrogenative coupling of amidine and alcohols

Inorganica Chimica Acta, Journal Year: 2025, Volume and Issue: unknown, P. 122678 - 122678

Published: March 1, 2025

Language: Английский

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Sustainable synthesis of pyrazoles using alcohols as the primary feedstock by an iron catalyzed tandem C–C and C–N coupling approach

Organic Chemistry Frontiers, Journal Year: 2022, Volume and Issue: 9(19), P. 5246 - 5258

Published: Jan. 1, 2022

We report two new efficient iron-catalyzed synthetic strategies for multicomponent synthesis of tri-substituted pyrazoles using biomass-derived alcohols as the primary feedstock.

Language: Английский

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