Alkene versus alkyne reactivity in unactivated 1,6-enynes: regio- and chemoselective radical cyclization with chalcogens under metal- and oxidant-free conditions

Green Chemistry, Journal Year: 2020, Volume and Issue: 22(7), P. 2288 - 2300

Published: Jan. 1, 2020

Substituted pyrrolidine derivatives are obtained via regio- and chemoselective 5-exo-dig radical cyclization of unactivated 1,6-enynes with chalcogens under metal- oxidant-free conditions.

Language: Английский

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Ethylene Glycol: A Green Solvent for Visible Light‐Promoted Aerobic Transition Metal‐Free Cascade Sulfonation/Cyclization Reaction

Advanced Synthesis & Catalysis, Journal Year: 2020, Volume and Issue: 362(13), P. 2609 - 2614

Published: May 1, 2020

Abstract With ethylene glycol as a green solvent, general transition metal‐free photocatalytic system using 9‐mesityl‐10‐methylacridinium perchlorate (Acr + −Mes ⋅ ClO 4 − ) catalyst was developed for the synthesis of sulfone‐containing heterocycles including thioflavones, oxindoles, and quinoline‐2,4(1 H ,3 )‐diones through cascade sulfonation/cyclization reactions under irradiation blue light at room temperature. magnified image

Language: Английский

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Electrosynthesis of 1-indanones

Chinese Chemical Letters, Journal Year: 2021, Volume and Issue: 32(5), P. 1591 - 1592

Published: March 6, 2021

Language: Английский

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Recent Advances in Cyclization Reactions of 1,6‐Enynes

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(6), P. 1220 - 1268

Published: Jan. 22, 2024

Abstract Elaborated molecular architectures, specifically those bearing one or more carbon stereocenters, stand as an important class of carbocyclic and heterocyclic frameworks because they are frequently occurring core structures in numerous natural products biologically active pharmaceutical molecules. Over the past few decades, development versatile synthetic approaches via cascade cyclization reactions 1,6‐enynes for construction a series fused spiro compounds has been focus great deal research initiatives. These synthesis strategies peculiarly fascinating context assembly wide array molecules, products, agrochemicals, functional materials. In this review, recent developments transformations with diverse coupling reagents summarized since 2018, which could be divided into five categories: 1) Introduction; 2) Transition metal catalyzed 1,6‐enynes; 3) Metal‐free 4) Visible‐light‐induced 5) Electrocatalytic 1,6‐enynes.

Language: Английский

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Photocatalytic Thio/Selenosulfonylation–Bicyclization of Indole-Tethered 1,6-Enynes Leading to Substituted Benzo[c]pyrrolo[1,2,3-lm]carbazoles

Organic Letters, Journal Year: 2024, Volume and Issue: 26(18), P. 3828 - 3833

Published: April 29, 2024

The photocatalyzed radical-triggered thio/selenosulfonylation–bicyclization of indole-tethered 1,6-enynes has been established for the first time, enabling synthesis various previously unreported thio/selenosulfonylated benzo[c]pyrrolo[1,2,3-lm]carbazoles with moderate to good yields under mild conditions. reaction pathway was proposed, consisting energy transfer, homolytic cleavage, radical addition, 5-exo-dig, coupling, and a Mallory cascade. This approach exhibits wide substrate compatibility excellent tolerability toward functional groups is characterized by its remarkable efficiency in both bond formation annulation.

Language: Английский

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Reversible Radical Addition Guides Selective Photocatalytic Intermolecular Thiol‐Yne‐Ene Molecular Assembly

Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: 63(13)

Published: Jan. 19, 2024

Abstract In modern organic chemistry, harnessing the power of multicomponent radical reactions presents both significant challenges and extraordinary potential. This article delves into this scientific frontier by addressing critical issue controlling selectivity in such complex processes. We introduce a novel approach that revolves around reversible addition thiyl radicals to multiple bonds, reshaping landscape reactions. The key lies intricate interplay between reversibility energy landscapes governing C−C bond formation thiol‐yne‐ene developed not only allows prioritize cascade, dominating over alternative reactions, but also extends scope coupling products obtained from alkenes alkynes various structures electron density distributions, regardless their relative polarity difference, opening doors more versatile synthetic possibilities. present study, we provide powerful tool for atom‐economical C−S formation, paving way efficient synthesis molecules. Carrying out our experimental computational studies, elucidated fundamental mechanisms underlying cascades, knowledge can be broadly applied field chemistry.

Language: Английский

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Radical-Triggered Bicyclization and Aryl Migration of 1,7-Diynes with Diphenyl Diselenide for the Synthesis of Selenopheno[3,4-c]quinolines

Organic Letters, Journal Year: 2025, Volume and Issue: 27(4), P. 1000 - 1005

Published: Jan. 17, 2025

The translocation of an aryl group from selenium into carbon enabled by the cleavage C-Se bond is reported using nitrogen atom-linked 1,7-diynes and diaryl diselenides as starting materials, leading to various selenophene derivatives in a regioselective manner. This method enables construction two bonds C-C through sequential radical bicyclization 1,2-aryl migration under metal-free conditions. Control experiments mechanistic studies suggest that this reaction proceeds inert C(Ph)-Se bond, facilitating process. transformation one-step conversion simple diverse selenopheno[3,4-c]quinolines via radical-promoted process, holding significant potential for new seleniferous heterocycles.

Language: Английский

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Cu(OTf)₂-mediated C(sp²)–H arylsulfonylation of enamides via the insertion of sulfur dioxide

Organic Chemistry Frontiers, Journal Year: 2018, Volume and Issue: 6(1), P. 94 - 98

Published: Nov. 23, 2018

A stereoselective Cu(OTf)₂-mediated C(sp²)–H sulfonylation of enamides with arylsulfonyl radicals generated in situ from DABSO and diazonium salts is developed.

Language: Английский

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Copper-catalyzed one-pot three-component thioamination of 1,4-naphthoquinone

Organic Chemistry Frontiers, Journal Year: 2019, Volume and Issue: 6(9), P. 1476 - 1480

Published: Jan. 1, 2019

A concise one-pot three-component thioamination of 1,4-naphthoquinone with thiols and amines was developed to synthesize 2-amino-3-thio-1,4-naphthoquinones.

Language: Английский

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Regioselective synthesis of polycyclic sulfonesviaradical-induced three-component bicyclization cascades

Chemical Communications, Journal Year: 2019, Volume and Issue: 55(22), P. 3227 - 3230

Published: Jan. 1, 2019

New radical-triggered three-component bicyclization cascades of 2-alkynyl aryldiazonium tetrafluoroborates with a sulfur dioxide surrogate DABCO·(SO2)2 and internal alkynes such as haloalkynes ynones have been reported for the first time, leading to 49 examples polycyclic sulfones moderate good yields high levels regioselectivity. This transformation initiated by an in situ generated arylsulfonyl radical proceeds efficiently under mild neutral redox conditions, which provide easy metal-free pathway toward formation range richly decorated indeno[1,2-c]thiochromene 5,5-dioxides.

Language: Английский

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