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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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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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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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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Electrochemical N‐Centered Radical‐Triggered Intramolecular N‐N Coupling for the Cyclization of o‐Aminyl Azobenzenes

European Journal of Organic Chemistry, Год журнала: 2024, Номер 27(46)

Опубликована: Авг. 28, 2024

Abstract An electrochemical radical cyclization of o ‐aminyl azobenzenes via N ‐centered generation has been developed for the synthesis benzotriazoles. The bearing a sulfonyl protection on amine readily proceeds in absence any external transition metal catalyst or chemical oxidant, and exhibits good tolerance towards functional groups.

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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Five-membered ring systems: With more than 1 N atom

Progress in heterocyclic chemistry, Год журнала: 2024, Номер unknown, С. 211 - 257

Опубликована: Янв. 1, 2024

Язык: Английский

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