Recent advances on cross-coupling of alcohols via borrowing hydrogen catalysis

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(30), P. 4002 - 4014

Published: Jan. 1, 2024

This article highlights the recent advances and significance of β-alkylation reactions towards synthesis higher order alcohols.

Language: Английский

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Designing Cobalt(II) Complexes for Tandem Dehydrogenative Synthesis of Quinoline and Quinazoline Derivatives

Organic Letters, Journal Year: 2024, Volume and Issue: 26(2), P. 514 - 518

Published: Jan. 9, 2024

In this work, we have constructed three new Co(II) complexes in which steric features govern their structural geometry. The metal ligand-cooperation behavior of the alkoxy arm is utilized to explore catalytic activities these with respect dehydrogenation. A wide range C-3-substituted quinoline and quinazoline derivatives were synthesized high yields. developed protocol's usefulness enhanced by chemoselective transformation different fatty alcohols synthesize heterocycles having distal unsaturation. Various kinetic, mechanistic, control studies conducted comprehend reaction route.

Language: Английский

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Direct Synthesis of Gem-β,β′-Bis(alkyl) Alcohols Using Nickel Catalysis via Sequential DCR Approach

ACS Catalysis, Journal Year: 2024, Volume and Issue: 14(6), P. 4018 - 4029

Published: Feb. 28, 2024

Chemoselective synthesis of functionalized gem-β,β′-bis(alkyl)alcohols by coupling a β-alkylated secondary alcohol with primary is reported using nickel via sequential DCR (dehydrogenation–condensation–rehydrogenation) approach. Using our method, 1-arylethanol and benzyl alcohols undergo one-pot successive double alkylation reaction to form alcohols. Methanol, C2–C12 alcohols, citronellol, fatty acid-derived oleic are tolerated, including late-stage functionalization steroid hormones (cholesterol testosterone) 5-pregnen-3β-ol-20-one. The catalytic transformations enabled the donepezil drug (used for Alzheimer's disease), N-heteroarenes (quinoline acridine), chromane intermediate flavan derivatives. Hammett kinetic plot analysis differently p-substituted 1-phenyl propanol indicated that oxidation might be rate-determining step expected strong influence substitution on kinetics. A negative ρ value (−0.60) strongly signify formation positive charge alcohol. Preliminary mechanistic investigation revealed dehydrogenation aldehyde as it involves C–H/D bond breaking alcohol, PH/PD 6.0 was calculated. Reaction profile studies, EPR experiments, Hammett-plot cyclic voltammetry, UV–visible XPS analysis, structural electronic changes at Ni-center well behavior catalysts during progress reactions.

Language: Английский

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Challenges and opportunities on sustainable electrochemical transformations: application towards the synthesis of pharmaceuticals and precursors of drug-like molecules

Green Chemistry, Journal Year: 2024, Volume and Issue: 26(10), P. 5770 - 5789

Published: Jan. 1, 2024

This article highlighted the recent demand for sustainable and resource efficient drug synthesis using electrochemical strategies.

Language: Английский

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Recent Advances in the Use of 2‐Aminobenzyl Alcohols in the Synthesis of Quinolines, Quinazolines and Other N‐Heterocycles

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(10), P. 2142 - 2164

Published: Jan. 17, 2024

Abstract N‐Heterocyclic compounds, in particular, quinolines and quinazolines are frequently used medicinal chemistry. Therefore, the direct clean synthesis of these valuable scaffolds has been a great interest for many years. 2‐Aminobenzyl alcohols as an alternative reactant instead unstable expensive 2‐aminobenzaldehydes can be construction N‐fused heterocycles including quinolines, quinazolines, oxazines, thiazines, selenazines, imidazoles, diazepines, etc. In this review article, we have discussed recent developments use 2‐aminobenzyl diverse heterocycles.

Language: Английский

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Ru-CNP Complex-Catalyzed Hydrogen Transfer/Annulation Reaction of 2-Nitrobenzylalcohol via an Outer-Sphere Mechanism

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: April 3, 2025

The development of efficient catalysts plays a central role in advancing chemical reactions. In this study, ruthenium complex modified with N-heterocyclic carbene-imine-phosphine ligand (CNP) was employed to enhance the hydrogen transfer/annulation process 2-nitrobenzyl alcohols various primary or secondary alcohols. NMR and HRMS analyses reaction solution revealed situ formation [fac-RuH(CO)(PPh3)(κ3-CN(H)P)]Cl through transfer hydrogenation imine moiety within CNP under conditions. This species, bifunctional Noyori-type featuring facial coordination CN(H)P ligand, served as key catalytic intermediate. By leveraging outer-sphere mechanism facilitated by [fac-RuH(CO)(PPh3)(κ3-CN(H)P)]Cl, synthesis 75 quinolines from wide range has been achieved yields high 95%.

Language: Английский

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<i>ortho</i>-Functionalized nitroarenes in the synthesis of heterocycles

Russian Chemical Reviews, Journal Year: 2025, Volume and Issue: 94(4), P. RCR5167 - RCR5167

Published: April 1, 2025

The development of convenient methods for the synthesis heterocyclic compounds that are highly important search pharmacological substances and in other spheres human activity is among most relevant fields organic chemistry. Two functional groups arenes located adjacent positions benzene ring can provide a fused ring. If at least one two <i>ortho</i>-functional contains nitrogen atom, heterocycle formed upon cyclization. nitro group often chosen as nitrogen-containing <i>ortho</i>-substituted to form systems, because ready availability <i>ortho</i>-functionalized nitroarenes, ability undergo various reactions selectivity reactions. This review integrates analyzes first time published data on involvement nitroarenes design structures. Using numerous examples reported literature last decade, mutually beneficial effect groups, which group, formation heterocycles demonstrated. Examples both intramolecular cyclizations involving additional reagents considered. gives holistic view potential functionalized <i>ortho</i>-nitroarenes systems. <br> bibliography includes 132 references.

Language: Английский

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Reaction of 2-Aminobenzyl Alcohols with β-Dicarbonyl Compounds to Synthesize Quinoline Derivatives in Water Promoted by Active Manganese Dioxide

Chinese Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 44(5), P. 1649 - 1649

Published: Jan. 1, 2024

Language: Английский

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Potent pincer-zinc catalyzed homogeneous α-alkylation and Friedländer quinoline synthesis reaction of secondary alcohols/ketones with primary alcohols

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(31), P. 6393 - 6408

Published: Jan. 1, 2024

Herein, we describe an air- and moisture-stable, homogeneous zinc catalyst stabilised using electron deficient N^N^N pincer-type ligand.

Language: Английский

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Accessing 2‐Aryl Quinolines via Acceptorless Dehydrogenation and Transfer Hydrogenation Under Base and Solvent‐Free Reaction Conditions

ChemistrySelect, Journal Year: 2023, Volume and Issue: 8(45)

Published: Dec. 1, 2023

Abstract Catalytic hydrogenation/dehydrogenation reactions are one of the most active areas research for synthesis pharmaceuticals and fine chemicals. Despite several efficient homogeneous catalysts that have already been identified, highly heterogeneous remain elusive. Herein, we report an easy convenient wet impregnation method Pd‐nanoclusters supported on ZnO nanoparticles. The catalyst displays a multifunctional role in 2‐aryl quinolines using alcohol 2‐nitrobenzyl as reactants via dehydrogenation/hydrogenation pathway under neat base‐free reaction conditions. exhibits excellent selectivity can be recycled five times without appreciable loss its activity.

Language: Английский

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