Multiple-fold C–F bond functionalization for the synthesis of (hetero)cyclic compounds: fluorine as a detachable chemical handle

Organic Chemistry Frontiers, Год журнала: 2022, Номер 9(7), С. 2013 - 2055

Опубликована: Янв. 1, 2022

We highlighted the recent advances in field of multiple-fold C–F bond functionalization for synthesis (hetero)cyclic compounds.

Язык: Английский

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Single-atom skeletal editing of 2H-indazoles enabled by difluorocarbene

Science China Chemistry, Год журнала: 2023, Номер 66(7), С. 1975 - 1981

Опубликована: Май 11, 2023

Язык: Английский

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Mechanochemical Synthesis of 1,2-Diketoindolizine Derivatives from Indolizines and Epoxides Using Piezoelectric Materials

Organic Letters, Год журнала: 2021, Номер 23(18), С. 7171 - 7176

Опубликована: Авг. 30, 2021

A simple and efficient mechanochemical-induced approach for the synthesis of 1,2-diketoindolizine derivatives has been developed. BaTiO3 was used as piezoelectric material in this transformation. This method features no usage solvent, experimental operation, scalable potential, high conversion efficiency, which make it attractive practical.

Язык: Английский

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B₂pin₂-Mediated Cascade Cyclization/Aromatization Reaction: Facial Access to Functionalized Indolizines

Organic Letters, Год журнала: 2022, Номер 24(40), С. 7372 - 7377

Опубликована: Сен. 29, 2022

Herein, a B2pin2-mediated radical cascade cyclization/aromatization reaction of enaminone with pyridine is described. This strategy provides practical way for the construction valuable functionalized indolizines under metal-, external oxidant-, and base-free conditions, which could be compatible various kinds functional groups, such as halogen, π-system, heterocycle, ferrocenyl, etc. A preliminary mechanism investigation indicated that pyridine-boryl formed in situ triggered to occur.

Язык: Английский

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Mechanochemically Induced Dehydrogenation Coupling and [3+2] Cycloaddition of Indolizines with Allenes Using Piezoelectric Materials

The Journal of Organic Chemistry, Год журнала: 2022, Номер 87(5), С. 3265 - 3275

Опубликована: Янв. 26, 2022

A wide range of indolizines with allenes proceeded smoothly under mechanochemically induced conditions via a [3+2] annulation process, affording various substituted pyrrolo[2,1,5-cd]indolizines in good yields. The reaction efficiency was greatly improved by using piezoelectric material as the charge transfer catalyst. photophysical properties resulting pyrrolo[2,1,5-cd]indolizine were characterized.

Язык: Английский

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Metal-free synthesis of gem-difluorinated heterocycles from enaminones and difluorocarbene precursors

Chemical Communications, Год журнала: 2022, Номер 58(21), С. 3477 - 3480

Опубликована: Янв. 1, 2022

A cascade strategy to synthesise gem-difluorinated 2H-furans from reactions of BrCF2CO2Et with enaminones has been described. The tolerate a wide variety functional groups under metal-free conditions. An active aminocyclopropane is proposed be key intermediate through the cyclopropanation difluorocarbene enaminones, which further triggers regioselective C-C bond cleavage in situ afford corresponding 2H-furans.

Язык: Английский

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Synthesis of Indolizines via Tf₂O-Mediated Cascade Reaction of Pyridyl-enaminones with Thiophenols/Thioalcohols

Organic Letters, Год журнала: 2023, Номер 25(7), С. 1192 - 1197

Опубликована: Фев. 13, 2023

A cost-effective, highly regioselective and metal-free version for the synthesis of indolizine derivatives by means Tf2O-mediated cascade reaction pyridyl-enaminones thiophenols/thioalcohols under mild conditions has been reported. Diverse electron-rich could be obtained in up to 94% yield via selective 1,4-addition vinyl iminium triflate tandem cyclization/aromatization, which allowed simultaneous construction C–N C–S/and one example C–Se bonds.

Язык: Английский

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Electro-Oxidative sp³ C–H Bond Functionalization and Annulation Cascade: Synthesis of Novel Heterocyclic Substituted Indolizines

The Journal of Organic Chemistry, Год журнала: 2022, Номер 87(5), С. 2898 - 2911

Опубликована: Фев. 1, 2022

Indolizine derivatives are prevalent in many synthetic intermediates, pharmaceuticals, and organic materials. Herein, we report a novel electro-oxidative cascade cyclization reaction that uses electricity as the primary energy input to promote reaction, leading series of heterocyclic substituted indolizine under exogenous-oxidant-free conditions. It is noteworthy this electrochemical method provides strategy for generating diversity quinazolinones quinolines on indolizines. In addition, sole byproduct was molecular hydrogen.

Язык: Английский

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Pyridinium Ylide-Mediated Diastereoselective Synthesis of Spirocyclopropanyl-pyrazolones via Cascade Michael/Substitution Reaction

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(11), С. 8230 - 8242

Опубликована: Май 14, 2024

We have devised a highly diastereoselective formal [2 + 1] annulation reaction of arylidene/alkylidine-pyrazolones with in situ-generated supported as well standard pyridinium ylides to construct spirocyclopropanyl-pyrazolones. The cascade approach exhibits wide range functional group tolerance, gram-scale capability, and substrate versatility. A diverse spirocyclic cyclopropanes was synthesized extensively both mediators, the pyridine reused subsequent cycles. Density theory calculations confirmed formation spirocyclopropane lower energy pathway.

Язык: Английский

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Base-controlled selective cleavage of the C–F bond of difluorocarbene for the divergent assembly of indolizines

Organic Chemistry Frontiers, Год журнала: 2024, Номер 11(15), С. 4214 - 4218

Опубликована: Янв. 1, 2024

A [3 + 1 1] cascade annulation reaction for the divergent construction of trisubstituted indolizines using sulfoxonium ylides, BrCF 2 CO Me and pyridinium salts as readily available substrates has been developed.

Язык: Английский

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