Multicomponent Synthesis of Alkyl BCP-Heteroaryls via Electron Donor–Acceptor Complex Photoactivation under Mild Conditions

The Journal of Organic Chemistry, Год журнала: 2025, Номер 90(4), С. 1683 - 1696

Опубликована: Янв. 17, 2025

In the vanguard of sustainable chemistry, pursuit efficient pathways for synthesis alkyl bicyclo[1.1.1]pentane-heteroaryls has captured attention scientific vanguard. We herein report a groundbreaking and eco-conscious multicomponent coupling reaction that paves way alkylation heteroarylation [1.1.1]propellane, process uniquely enabled by photochemical prowess an electron donor–acceptor (EDA) complex. This method is distinguished its minimalist yet powerful approach: devoid transition metals, additives, photosensitizers. Its universality further exemplified seamless compatibility broad spectrum halides heteroarenes under standardized conditions, heralding new era synthetic versatility. The method's practicality underscored capacity late-stage modification pharmaceuticals, offering transformative tool enhancement existing drug molecules. Moreover, facile derivatization synthesized products underscores adaptability potential diverse applications. Our mechanistic studies have elucidated underlying radical-relay pathway, pinpointing pivotal role EDA complex in initiating transformation. discovery not only enriches our fundamental understanding but also opens avenues strategic optimization.

Язык: Английский

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Visible photons as ideal reagents for the activation of coloured organic compounds

Chemical Society Reviews, Год журнала: 2024, Номер 53(10), С. 4926 - 4975

Опубликована: Янв. 1, 2024

In search for the perfect wave(length). This review is dedicated to recent efforts in development of visible light driven photochemical strategies occurring coloured organic compounds.

Язык: Английский

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Transition-metal-, oxidant- and additive-free multi-component synthesis of alkyl heteroaryl BCPs enabled by visible-light-induced phosphine-catalyzed halogen-atom transfer

Organic Chemistry Frontiers, Год журнала: 2024, Номер unknown

Опубликована: Янв. 1, 2024

This study describes a pioneering visible-light-induced phosphine-catalyzed halogen-atom transfer (XAT) strategy that heralds new era in the difunctionalization of [1.1.1]propellane.

Язык: Английский

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Photocatalyzed 1,3-Bromodifluoroallylation of [1.1.1]Propellane with α-Trifluoromethylalkenes and KBr Salts

Organic Letters, Год журнала: 2024, Номер 26(32), С. 6889 - 6893

Опубликована: Авг. 6, 2024

Herein we unveil a visible-light-driven transition-metal-free 1,3-bromodifluoroallylation of [1.1.1]propellane. This reactivity is harnessed through organophotocatalysis, providing practical synthetic pathways to 1-brominated-3-

Язык: Английский

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Photoinduced Multicomponent Heteroarylation of [1.1.1]Propellane with Katritzky Pyridinium Salts

Organic Letters, Год журнала: 2024, Номер 26(33), С. 7026 - 7030

Опубликована: Авг. 14, 2024

(Hetero)arylated bicyclo[1.1.1]pentanes (BCPs) are important for the construction of complex druglike target molecules. Herein, we developed a method light-induced, Cs

Язык: Английский

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Photoinduced rapid Chloropropylation of Quinoxalin-2(1H)-ones with Cyclopropane and HCl

Molecular Catalysis, Год журнала: 2024, Номер 558, С. 114024 - 114024

Опубликована: Март 18, 2024

Язык: Английский

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EDA Complex from BCP‐Thianthrenium Salt: A Catalyst‐free Strategy To Access 1‐Trifluoromethyl‐3‐quinoxaline Derivatives Bicyclo[1.1.1]pentanes

European Journal of Organic Chemistry, Год журнала: 2024, Номер 27(27)

Опубликована: Май 13, 2024

Abstract The construction of bicyclo[1.1.1.]pentanes (BCPs) typically require the cumbersome use labile [1.1.1.]propellane in solution and involve multicomponent radical reactions, which commonly produce undesired by‐products that hinder efficient BCPs. In this paper, we present a catalyst‐free strategy by constructing an electron donor‐acceptor (EDA) complex utilizing naturally electron‐deficient nature BCP thianthrenium salt, were irradiated with visible light to obtain trifluoromethyl‐BCP radicals through SET process, subsequently reacted various substituted quinoxalines. Moreover, successful structural modification drug molecule derivatives confirm utility scheme field discovery.

Язык: Английский

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Recent Advances in Radical Coupling Reactions Directly Involving Bicyclo[1.1.1]pentane (BCP)

Topics in Current Chemistry, Год журнала: 2025, Номер 383(1)

Опубликована: Янв. 18, 2025

Язык: Английский

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Photoredox/Copper Cooperatively Catalyzed Arylalkynylation of [1.1.1]Propellane

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Март 20, 2025

We present a sp2–sp3/sp3–sp bond formation reaction through three-component coupling strategy involving terminal alkynes, [1.1.1]propellane, and aryl thianthrenium salts that are prepared from arenes. The employs dual photo/copper catalysis system provides streamlined approach for assembling 1-alkynyl-3-aryl bicyclo[1.1.1]pentane derivatives with broad spectrum of functional group compatibility. Mechanistic studies suggest the generation radicals copper alkynide intermediates was involved.

Язык: Английский

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Electrochemical C–H silylation of azauracils with hydrosilanes

Molecular Catalysis, Год журнала: 2025, Номер 583, С. 115218 - 115218

Опубликована: Май 24, 2025

Язык: Английский

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