Catalytic Generation of Pyridyl Radicals via Electron Donor–Acceptor Complex Photoexcitation: Synthesis of 2-Pyridylindole-Based Heterobiaryls

Organic Letters, Год журнала: 2024, Номер unknown

Опубликована: Сен. 17, 2024

We report the catalytic generation of pyridyl radicals through photoexcitation electron donor-acceptor (EDA) complex, which enables C2-selective heteroarylation indole under ambient conditions. In this manifold, triarylamine and chloropyridine aggregate into an EDA complex in presence inorganic base, making readily available chloropyridines good precursors for diverse radicals. Given broad reaction scope, protocol provides robust access to heterobiaryl scaffolds that are widely present biologically important molecules.

Язык: Английский

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Dearomative Functionalization of Activated Quinolines: Transfer Hydrogenation/Cycloaddition Cascade to Construct α‐Tertiary Amines

Advanced Synthesis & Catalysis, Год журнала: 2024, Номер 366(20), С. 4219 - 4227

Опубликована: Авг. 7, 2024

Abstract Cascade dearomative functionalization is a robust protocol to convert flat arenes into medicinally relevant three‐dimensional architectures with added new functionality. Herein, cycloaddition for synthesizing tetrahydroquinoline‐embedded α‐tertiary amine scaffolds has been developed employing quinolinium salts and sulfonyl azides under metal‐free conditions. An underexplored mechanistically distinct pathway unveiled, creating quaternary‐center‐bearing skeletons by an group migration during the transfer hydrogenation cascade reaction. This approach provided broad substrate scope of from plethora C3‐substituted azides. The post‐synthetic modifications have further diversified core interesting scaffolds. Preliminary mechanistic studies suggested involvement aziridine ring formation C‐3 position quinoline generate core.

Язык: Английский

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A Regiodivergent Dearomative Trifunctionalization of Quinolinium Salts to Access Fused Tetrahydroquinoline Polycycles

Organic Letters, Год журнала: 2024, Номер 26(34), С. 7144 - 7148

Опубликована: Авг. 19, 2024

Dearomative trifunctionalization of quinolinium salts is one the most straightforward approaches to access biologically relevant multisubstituted tetrahydroquinolines. However, research in this field still its infancy. Here, we report a base-controlled regiodivergent dearomative strategy for transforming quinoliniums into two kinds structurally intriguing tetrahydroquinoline polycycles through one-pot three-component cascade annulation. The key situ generation "Nu–E–Nu" trifunctional reagent that can precisely identify matched reactive sites quinoliniums.

Язык: Английский

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Diastereoselective dearomative bifunctionalization of isoquinolinium salts to access bridged tetrahydroisoquinolines

New Journal of Chemistry, Год журнала: 2024, Номер 48(37), С. 16151 - 16154

Опубликована: Янв. 1, 2024

We report a diastereoselective dearomative bifunctionalization strategy of using isoquinolinium salts to access bridged tetrahydroisoquinolines through one-pot three-component cascade process.

Язык: Английский

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Ruthenium-Catalyzed Interrupted Transfer Hydrogenation: An Approach for Reductive Functionalization of Quinolinium and Napthyridinium Salts

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(18), С. 13167 - 13178

Опубликована: Сен. 11, 2024

Until now, a myriad of effective approaches have emerged for the functionalization

Язык: Английский

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Dearomative Transformation of Pyridin-3-ols into 2,3,6,7-Tetrahydro-1H-2,6-methanobenzo[d]azonin-12-ones via Oxidopyridinium/o-Quinodimethane (5 + 4) Cycloaddition

Organic Letters, Год журнала: 2024, Номер unknown

Опубликована: Дек. 23, 2024

We report the dearomative transformation of pyridin-3-ols via oxidopyridinium (5 + 4) cycloaddition with o-quinodimethanes, leading to 2,3,6,7-tetrahydro-1H-2,6-methanobenzo[d]azonin-12-ones. The chemoselective derivatization obtained cycloadduct was also investigated demonstrate synthetic potential cycloadduct.

Язык: Английский

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