A comprehensive review on synthesis of oxazoles: research on magnetically recoverable catalysts

Research on Chemical Intermediates, Journal Year: 2024, Volume and Issue: 50(4), P. 1845 - 1872

Published: March 9, 2024

Language: Английский

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Empowering boronic acids as hydroxyl synthons for aryne induced three-component coupling reactions

Chemical Science, Journal Year: 2023, Volume and Issue: 14(16), P. 4278 - 4287

Published: Jan. 1, 2023

Boronic acids as a tunable hydroxy source display unique reactivity paradigm through hitherto unknown aryne-induced multicomponent reactions.

Language: Английский

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Recent Advancements in Strategies for the Synthesis of Imidazoles, Thiazoles, Oxazoles, and Benzimidazoles

ChemistrySelect, Journal Year: 2023, Volume and Issue: 8(47)

Published: Dec. 13, 2023

Abstract Nitrogen‐containing heterocycles such as imidazoles, thiazoles, and oxazoles play a significant role in the fields of biological pharmaceutical chemistry. These compounds were widely used for agrochemical, pesticide, medicinal, industrial applications. Due to wide spectrum structural diversity well activity N ‐heterocycles, plethora reports on their synthesis have appeared last few decades. However, developments various bond‐forming strategies C−C, C−N, C−O, C−S, N−N, C−H activation, been powerful synthetic tool derive copious ‐heterocycles. The most prominent fascinating imidazole, thiazole, oxazoles, benzimidazole moieties by C−C C−N coupling reactions, multi‐component cycloaddition etc. are discussed this study. studies demonstrated enormous potential methods accelerating modern chemical establishing molecular beauty through bonding. aspects methodologies, like optimized conditions, substrate scope, mechanistic investigations, detail.

Language: Английский

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Selective S-Arylation of Sulfenamides with Arynes: Access to Sulfilimines

Organic Letters, Journal Year: 2023, Volume and Issue: 25(39), P. 7192 - 7197

Published: Sept. 21, 2023

Sulfilimines, the aza analogues of sulfoxides, are increasing interest in medicinal and agrochemical research programs. However, development efficient routes for their synthesis has remained relatively unexplored. In this study, we report a transition metal-free, selective S-arylation reaction between sulfenamides arynes, enabling facile preparation structurally diverse sulfilimines under mild redox-neutral conditions good yields. The application value our method was further demonstrated by scale-up synthesis, downstream derivatization, robustness screen.

Language: Английский

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Aryne‐Enabled C−N Arylation of Anilines

Angewandte Chemie International Edition, Journal Year: 2023, Volume and Issue: 62(49)

Published: Oct. 18, 2023

Abstract Anilines are potentially high‐value arylating agents, but limited by the low reactivity of strong C−N bond. We show that reactive intermediate benzyne can be used to both activate anilines, and set‐up an aryl transfer reaction in a single step. The does not require any transition metal catalysts or stoichiometric organometallics, establishes metal‐free route valuable biaryl products functionalizing aniline

Language: Английский

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Green Synthesis of α-Keton Thiol Ester via Photocatalytic Oxidative Radical Addition of Thioic Acid to Alkene

Organic Letters, Journal Year: 2023, Volume and Issue: 25(22), P. 4173 - 4176

Published: May 30, 2023

α-Keton sulfides are versatile building blocks in organic synthesis. From thioic acids and alkenes, we were able to develop the direct synthesis of α-keton thiol esters via photocatalytic oxidative radical additions. This reaction well matches idea green chemistry. It takes advantage thioxanthone as an inexpensive photocatalyst, O2 a oxidant, EtOAc solvent, visible light sustainable energy source, only byproduct is water.

Language: Английский

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Regiodivergent Synthesis of 4‐ and 5‐Sulfenyl Oxazoles from Alkynyl Thioethers

Chemistry - A European Journal, Journal Year: 2024, Volume and Issue: 30(40)

Published: May 14, 2024

The regiodivergent synthesis of 4- and 5-sulfenyl oxazoles from 1,4,2-dioxazoles alkynyl thioethers has been achieved. Gold-catalysed conditions are used to favour the formation via β-selective attack nitrenoid relative sulfenyl group. In contrast, 4-sulfenyl formed by α-selective reaction under Brønsted acid same substrates. nature stabilising gold-sulfur interactions have investigated natural bond orbital analysis, showing that S→Au significantly stronger in intermediate favours oxazoles. A kinetic survey identifies catalyst inhibition processes. This study into methods includes development telescoped annulation-oxidation protocols for regioselective access oxazole sulfoxides sulfones.

Language: Английский

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Divergent Construction of α,α-Difunctionalized Ketones via [1,2]-Sigmatropic Rearrangement/Alkylation-Hydroxylation/Dialkylation of I^(III)/S^(VI) Ylides

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: April 1, 2025

The rare [1,2]-sigmatropic rearrangement of sulfoxonium-iodonium hybrid ylides is described, which enables the efficient sulfoxidation/sulfonylation-alkylation I(III)/S(VI) with 1,3-dicarbonyls. By slight modification reaction conditions, controllable alkylation-hydroxylation and dialkylation were achieved. This strategy affords a diverse array α,α-difunctionalized ketones in moderate to good yields, demonstrating broad substrate scope. These findings provide an important advancement sulfoxonium highlight divergent reactivity ylides.

Language: Английский

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Access to N-Aryl (Iso)quinolones via Aryne-Induced Three-Component Coupling Reaction

Organic Letters, Journal Year: 2024, Volume and Issue: 26(9), P. 1840 - 1844

Published: Feb. 27, 2024

N-Aryl (iso)quinolones are of increasing interest in material and medicinal chemistry, although general routes for their provision remain underexplored, especially when compared with its N-alkyl counterparts. Herein, we report a modular transition-metal-free, aryne-induced three-component coupling protocol that allows the facile synthesis structurally diverse N-aryl from readily accessible halo-(iso)quinolines presence water. Preliminary results highlight applicability our method through scale-up synthesis, downstream derivatization, flexible involving other types aryne precursors.

Language: Английский

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Tunable Electrochemical Diverse Sulfurization of Sulfoxonium Ylides with Disulfides

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(65), P. 8573 - 8576

Published: Jan. 1, 2024

An electrochemical protocol for the synthesis of sulfursulfoxonium ylides and 1,3-dithioketals by reacting sulfoxonium with disulfides has been developed under simple mild conditions. By changing solubility raw materials dielectric parameters electrolyte, sulfurization enabled a selective dehydrogenation C-S construction 1,3-dithioketals. The transformation is an ideal approach to prepare organosulfur reagents broad functional group tolerance as well high selectivity, which leads vicinal difunctionalized compounds.

Language: Английский

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