Photoactive Arylamine Appended β‐Naphthols via Friedel–Crafts Alkylation of Vinylidine Quinone Methides (VQMs)

Chemistry - An Asian Journal, Год журнала: 2025, Номер unknown

Опубликована: Апрель 16, 2025

Abstract Substituted naphthol derivatives have received significant attention due to their wide range of biological and pharmaceutical activities, further extending the generation with photoactive materials promotes optoelectronic applications. Nevertheless, synthetic methodology such hitherto unknown. In this study, we adopted an efficient Friedel–Crafts reaction ortho ‐alkynylnaphthols N,N ‐disubstituted arylamines generate arylamine‐appended β‐naphthol derivatives. This transformation features broad substrate scope, excellent yields, high atom economy method was successfully adapted for late‐stage functionalization biomolecules drug molecules yields. Further, UV–vis absorption emission studies reveal that these shown visible blue a quantum efficiency 10%. Lately, photo‐irradiation on arylamine leads charged state facilitates improvement electronic properties. Consequently, novel paves way new developments in area small molecule‐derived optoelectronics.

Язык: Английский

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Chiral Brønsted Acid‐Catalyzed Asymmetric Reaction via Vinylidene Ortho‐Quinone Methides

Chemistry - A European Journal, Год журнала: 2024, Номер 30(49)

Опубликована: Июнь 26, 2024

Vinylidene ortho-quinone methides (VQMs) have been proven to be versatile and crucial intermediates in the catalytic asymmetric reaction last decade, thus drawn considerable concentrations on account of practical application construction enantiomerically pure functional organic molecules. However, comparison well established chiral Brønsted base-catalyzed via VQMs, acid-catalyzed is rarely studied there no systematic summary date. In this review, we summarize recent advances VQMs according three types reactions: a) intermolecular nucleophilic addition VQMs; b) cycloaddition c) intramolecular cyclization VQMs. Finally, put forward remained challenges opportunities for potential breakthroughs area.

Язык: Английский

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Electrochemical domino sulfonylation/dearomative ipso‐annulation of 2‐alkynyl biaryls to access spiro(indenyl)cyclohexadienones

European Journal of Organic Chemistry, Год журнала: 2024, Номер unknown

Опубликована: Окт. 2, 2024

Abstract Herein, we present an efficient strategy for the synthesis of spiro(indenyl)cyclohexadienones through radical‐promoted reaction 2‐alkynyl biaryls with sodium sulfinates under electrochemical conditions. The involves sulfonylation and dearomative ipso‐ cyclisation in a domino fashion. This approach features use readily accessible precursors, wide functional group tolerance external oxidant‐free practicality method was also illustrated by scale‐up further diversification product.

Язык: Английский

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Organocatalyzed Enantioselective Double Dearomatization of Tricyclic Phenols and Alkoxybenzenes

Organic Letters, Год журнала: 2024, Номер unknown

Опубликована: Дек. 6, 2024

To advance more efficient dearomatization approaches, we present herein an organocatalyzed asymmetric double reaction of tricyclic phenols and alkoxybenzenes by leveraging a novel steric hindrance-regulated strategy for nonfunctionalized phenols. This protocol allows the synthesis structurally complex polycyclic diketones with four tertiary carbon centers under mild conditions while also showcasing potential multiple dearomatizations building intricate molecular frameworks from simple starting materials.

Язык: Английский

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Dearomative electrophilic spirocyclization via the intramolecular Ritter reaction: Diastereoselective access to hydrogenated spiroindolenines

Tetrahedron Letters, Год журнала: 2024, Номер 155, С. 155423 - 155423

Опубликована: Дек. 9, 2024

Язык: Английский

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