Visible Light-Mediated Heterodifunctionalization of Alkynylazobenzenes for 2H-Indazole Synthesis

Organic Letters, Год журнала: 2024, Номер 26(9), С. 1868 - 1873

Опубликована: Фев. 22, 2024

We disclose the heterodifunctionalization of alkynylazobenzenes promoted exclusively by visible light in absence any transition metal and/or photocatalyst. This reaction features excellent regioselectivity on a broad variety substrates with perfect atom economy. Alcohols, carboxylic acids, thiols, amides, heterocycles, and even water are suitable for promotion oxyamination, sulfenoamination, diamination reactions. In this manner, biologically active indazole scaffolds can be rapidly assembled from alkyne feedstocks.

Язык: Английский

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Electrochemical N(sp²)–H/C(sp³)–H cross-coupling reaction between sulfoximines and alkylarenes

Green Chemistry, Год журнала: 2024, Номер 26(10), С. 5824 - 5831

Опубликована: Янв. 1, 2024

An electrochemical oxidation-induced amination of simple alkylarenes with sulfoximines as a nitrogen source and 5,6-dimethyl-1 H -benzo[ d ]imidazole catalyst was developed.

Язык: Английский

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In‐situ Oxidation and Coupling of Anilines towards Unsymmetric Azobenzenes Using Flow Chemistry

ChemSusChem, Год журнала: 2024, Номер 17(10)

Опубликована: Янв. 19, 2024

Abstract Molecular switches, especially azobenzenes, are used in numerous applications, such as molecular solar thermal storage (MOST) systems and photopharmacology. The Baeyer‐Mills reaction of anilines nitrosobenzenes has been established an efficient synthetic method for non‐symmetric azobenzenes. However, not stable, depending on their substitution pattern pose a health risk. An in‐situ oxidation with Oxone® was optimized under continuous flow conditions avoiding isolation contact. generated nitrosobenzene derivatives were subjected to telescoped flow. That way azobenzenes broad substituent spectrum made accessible.

Язык: Английский

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Electrochemical Cyclization of o-Aminyl Azobenzenes: Roles of Aldehydes in N–N Bond Cleavage

Organic Letters, Год журнала: 2024, Номер 26(30), С. 6324 - 6329

Опубликована: Июль 22, 2024

Direct functionalization of azobenzenes provides an approach to obtaining valuable molecules in synthetic chemistry. However, efficient method for the cleavage N═N bond azobenzenes, which is a key process this transformation, still lacking. We herein disclose electrochemical reduction-induced cyclization with aldehydes via cleavage. This proceeds well absence any transition metals or external chemical oxidants, leading formation N-protected benzimidazoles moderate good yields.

Язык: Английский

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Visible‐light‐mediated synthesis of 2H-indazoles from (2-Bromo-benzylidene)-phenyl-amine derivatives by the Ullmann Goldberg reaction.

Tetrahedron, Год журнала: 2025, Номер unknown, С. 134486 - 134486

Опубликована: Янв. 1, 2025

Язык: Английский

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A General Strategy for C(sp³)─H Bond Etherification via Quinoline Derivative‐Mediated Electrolysis

Advanced Science, Год журнала: 2025, Номер unknown

Опубликована: Апрель 26, 2025

Abstract Electrooxidative coupling of C(sp 3 )─H bonds with nucleophiles offers an attractive method for constructing C─C and C─X without sacrificial oxidants. However, the direct electrochemical approach requires nucleophilic reagent to have a higher potential than partners, which restricts substrate scope. In this study, quinoline derivative is introduced as mediator, enabling efficient C─H bond etherification reduced reliance on electronic properties substrates. The catalytic system demonstrates broad compatibility, extending partners featuring diverse range bonds, including tertiary benzylic unactivated bonds. Mechanistic investigations confirm role electrocatalyst in hydrogen atom transfer (HAT) process. This provides versatile strategy late‐stage functionalization bioactive molecules.

Язык: Английский

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Electrochemical Oxidation of Primary Amines for the Synthesis of Benzimidazole, Benzothiazole, Quinazolinone, and Quinoxaline

The Journal of Organic Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Июнь 1, 2025

The development of green and efficient methods for the construction N-heterocyclic frameworks has attracted considerable attention in organic synthesis. In this work, an electrochemical oxidative cyclization primary amines synthesis benzimidazole, benzothiazole, quinazolinone, quinoxaline been developed. This catalyst- oxidant-free strategy demonstrates good functional group tolerance, up to 87% yield N-based heterocycles undivided cell under open-air conditions is easy scale up.

Язык: Английский

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Direct Deoxygenative C-N Coupling to Construct Indazole under Visible Light

Green Chemistry, Год журнала: 2024, Номер unknown

Опубликована: Янв. 1, 2024

The green synthesis of medicines with an indazole skeleton has gained significant attention in recent years.

Язык: Английский

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Photo- and Electro-chemical Strategies for Indazole Synthesis

Tetrahedron Chem, Год журнала: 2024, Номер unknown, С. 100116 - 100116

Опубликована: Дек. 1, 2024

The indazole core is prevalently found in the structures of bioactive molecules, demonstrating promising potential medicinal chemistry and drug discovery, which therefore has attracted sustained attention from synthetic community. Over recent decades, significant progress been achieved both organic photocatalysis electrosynthesis, offering novel approaches for efficient sustainable synthesis various functionalized indazoles. This mini-review highlights emerging methodological advancements photo-/electro-chemical two common forms indazole, namely 1H- 2H-indazoles, are classified by specific intramolecular bond formation patterns: (1) C-C formation, (2) C-N (3) N-N formation. reaction conditions, representative scopes, mechanistic understandings these protocols emphasized, to elucidate advantages limitations current strategies, with an aim inspire future innovations that may address challenges modern synthesis.Graphical abstractTo create your abstract, type over instructions template box below. Fonts or abstract dimensions should not be changed altered.

Язык: Английский

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Electrochemically Benzyl Cation‐Triggered Alkylacetoxylation of Terminal Alkynes and Carboxylic Acids

Advanced Synthesis & Catalysis, Год журнала: 2024, Номер 366(12), С. 2721 - 2727

Опубликована: Май 11, 2024

Abstract A catalyst‐free electrochemical alkylacetoxylation reaction of terminal alkynes with (thio)xanthenes and carboxylic acids is developed. Treating the addition products K 2 CO 3 as a base in methanol affords ketones moderate to good yields. Preliminary experimental computational studies indicate that benzylic cation generated from triggers electrophilic alkynes.

Язык: Английский

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