Recent advances in the synthesis of indolizine and its derivatives by radical cyclization/cross-coupling

Organic & Biomolecular Chemistry, Год журнала: 2021, Номер 19(47), С. 10245 - 10258

Опубликована: Янв. 1, 2021

The free-radical-induced syntheses of indolizines were reviewed by type catalyst.

Язык: Английский

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Recent Advances in Electrochemical Sulfonylation using Sodium Sulfinates as Sulfonyl Radical Precursors

Current Organic Chemistry, Год журнала: 2024, Номер 28(2), С. 105 - 116

Опубликована: Янв. 1, 2024

Abstract: Sodium sulfinates have been widely utilized as sulfonyl radical precursors for preparing a diverse array of value-added sulfur-containing compounds (sulfones, sulfonamides, sulfonates, thiosulfonates, etc.) through S-C, S-N, S-O and S-S bonds formation reactions. Organic electrosynthesis has become an attractive alternative to conventional methods redox reactions because it utilizes electric current instead chemical agents. As such, the electrochemical generation radicals from sodium their applications in organic attracted much attention. In this review, recent advances sulfonylation involving since 2015 were reviewed, along with related reaction mechanisms.

Язык: Английский

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Regioselective electrochemical cascade C–H sulfonylation–bromination of indolizines to access difunctionalized indolizines

Organic Chemistry Frontiers, Год журнала: 2024, Номер 11(8), С. 2306 - 2312

Опубликована: Янв. 1, 2024

Regioselective electrochemical C–H sulfonylation–bromination between indolizines, sodium sulfinates, and KBr has been established in an undivided cell, which serves as both the brominating agent electrolyte.

Язык: Английский

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Free Radical-Mediated Intramolecular Photocyclization of AIEgens Based on 2,3-Diphenylbenzo[b]thiophene S,S-Dioxide

Journal of the American Chemical Society, Год журнала: 2023, Номер 145(14), С. 7837 - 7844

Опубликована: Март 30, 2023

As an important category of photochemical reactions, photocyclization is regarded as ideal entry point for building intelligent photoresponsive materials. Herein, a series aggregation-induced emission luminogens (AIEgens) with sensitive behavior are developed based on 2,3-diphenylbenzo[b]thiophene S,S-dioxide (DP-BTO), and the impacts substituents different electronic structures investigated. The comprehensive experimental computational characterizations reveal that their activity resulted from triplet diradical-mediated intramolecular photocyclization, followed by dehydrogenation to yield stable polycyclic photoproducts. This process active in solution but suppressed solid state, thus can act supplementary nonradiative decay channel excited state contribute AIE effect. Moreover, generated diradical intermediates upon light irradiation effectively inhibit growth S. aureus, indicative promising application antibacterial agents. work provides in-depth mechanistic description about DP-BTO derivatives furnishes perspective correlation photophysical property.

Язык: Английский

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CH‐Functionalization of Heterocycles with the Formation of C−O, C−N, C−S/Se, and C−P Bonds by Intermolecular Addition of Heteroatom‐Centered Radicals

Advanced Synthesis & Catalysis, Год журнала: 2023, Номер 365(11), С. 1714 - 1755

Опубликована: Апрель 12, 2023

Abstract In the last decade, free radicals have found a wide application in functionalization of unsaturated compounds, such as alkenes, alkynes, and arenes, via free‐radical addition to carbon‐carbon π‐bonds. these processes, intermolecular attack on aromatic substrates represents challenge due relatively high resistance π‐system reactions comparison alkene C=C bonds. The heterocycles is especially interesting diversity their structures chemical properties well importance for medicinal chemistry, agrochemistry, materials science. Addition C‐centered widely known Minisci‐type well‐reviewed. this paper, we summarized main achievements less explored group processes: by heteroatom‐centered (O‐, N‐, S‐/Se‐, P‐radicals) with emphasis papers published after 2010. Literature analysis revealed strong trend towards usage electrochemistry photoredox‐catalysis generation recent years. remaining fundamental problem field lack experimental support proposed mechanisms frequent existence several plausible reaction pathways. progress mechanistic studies can significantly improve prediction optimal conditions depending structure.

Язык: Английский

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Thermodynamic Controlled Regioselective C1-Functionalization of Indolizines with 3-Hydroxyisoindolinones via Brønsted Acid Catalyzed aza-Friedel–Crafts Reaction

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(4), С. 2794 - 2799

Опубликована: Янв. 31, 2024

A Brønsted acid catalyzed aza-Friedel–Crafts reaction of indolizines with 3-hydroxyisoindolinones has been established, which constructs isoindolinone derivatives bearing a tetrasubstituted stereocenter in good to high yields and enantioselectivities. Notably, this strategy provides new access C1-functionalization excellent regioselectivities. Moreover, intriguing C1-regioselective transformation was induced under thermodynamic control.

Язык: Английский

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Controlled and Site-Selective C–H/N–H Alkenylation, Dialkenylation, and Dehydrogenative β-Alkenylation of Various N-Heterocycles

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(7), С. 4840 - 4850

Опубликована: Март 19, 2024

Here, we report controlled and site-selective C–H alkenylation dialkenylation of indolizines pyrrolo[1,2-a]quinolines with β-alkoxyvinyl trifluoromethylketones under simple practical conditions. Moreover, this direct strategy can also be extended to imidazo[1,2-a]pyridines. Notably, without a transition metal external oxidant, efficient dehydrogenative β-alkenylation tertiary amines is presented.

Язык: Английский

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Chiral Phosphoric Acid-Catalyzed Asymmetric Arylation of Indolizines: Atroposelective Access to Axially Chiral 3-Arylindolizines

Organic Letters, Год журнала: 2022, Номер 24(12), С. 2315 - 2320

Опубликована: Март 17, 2022

We report herein a highly straightforward strategy for the synthesis of new axially chiral 3-arylindolizine scaffold via organocatalytic asymmetric arylation reactions indolizines and p-quinone esters. Using phosphoric acid catalyst, series 3-arylindolizines were accessed in good to excellent yields atropo-enantioselectivities. This approach features broad substrate scope, mild reaction conditions, scalability, facile derivatization. Moreover, preliminary investigations based on nonlinear effects thermal racemization study demonstrated intrinsic pathway formation axial chirality its potential utility.

Язык: Английский

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Electrochemical nitration to synthesize 1,3,4- trinitropyrazole

Energetic Materials Frontiers, Год журнала: 2025, Номер unknown

Опубликована: Янв. 1, 2025

Язык: Английский

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Controlled Electrochemical C4 Sulfonylation of 1(2H)-isoquinolone derivatives: Through the isomerization of N-radical to C-radical

Tetrahedron, Год журнала: 2025, Номер 174, С. 134506 - 134506

Опубликована: Янв. 28, 2025

Язык: Английский

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