The application of azoarenes in the synthesis of nitrogen-containing heterocycles DOI
Azim Ziyaei Halimehjani,

Nima Sadeghzadeh,

S. MOGHADDAM

et al.

Tetrahedron, Journal Year: 2024, Volume and Issue: unknown, P. 134428 - 134428

Published: Dec. 1, 2024

Language: Английский

Visible Light-Mediated Heterodifunctionalization of Alkynylazobenzenes for 2H-Indazole Synthesis DOI Creative Commons
Clara Mañas, Estı́baliz Merino

Organic Letters, Journal Year: 2024, Volume and Issue: 26(9), P. 1868 - 1873

Published: Feb. 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.

Language: Английский

Citations

8
Electrochemical N(sp2)–H/C(sp3)–H cross-coupling reaction between sulfoximines and alkylarenes DOI

Qing‐Ru Zhu,

Peng-Zhan Zhang,

Xiang Sun

et al.

Green Chemistry, Journal Year: 2024, Volume and Issue: 26(10), P. 5824 - 5831

Published: Jan. 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.

Language: Английский

Citations

7
In‐situ Oxidation and Coupling of Anilines towards Unsymmetric Azobenzenes Using Flow Chemistry DOI Creative Commons
Jan H. Griwatz,

Chiara E. Campi,

Anne Kunz

et al.

ChemSusChem, Journal Year: 2024, Volume and Issue: 17(10)

Published: Jan. 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.

Language: Английский

Citations

5
Visible‐light‐mediated synthesis of 2H-indazoles from (2-Bromo-benzylidene)-phenyl-amine derivatives by the Ullmann Goldberg reaction. DOI
Ali Akbari,

Danial Zand Hosein shahi,

Ali Rahimabadi

et al.

Tetrahedron, Journal Year: 2025, Volume and Issue: unknown, P. 134486 - 134486

Published: Jan. 1, 2025

Language: Английский

Citations

0
A General Strategy for C(sp3)─H Bond Etherification via Quinoline Derivative‐Mediated Electrolysis DOI Creative Commons

Yousen Xu,

Hao Wu, Chenxi Zhu

et al.

Advanced Science, Journal Year: 2025, Volume and Issue: unknown

Published: April 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.

Language: Английский

Citations

0
Electrochemical Cyclization of o-Aminyl Azobenzenes: Roles of Aldehydes in N–N Bond Cleavage DOI
Anni Li,

Anna Gao,

K. K. N. CHEN

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(30), P. 6324 - 6329

Published: July 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.

Language: Английский

Citations

3
Direct Deoxygenative C-N Coupling to Construct Indazole under Visible Light DOI

Xinluo Song,

Lingfeng Yin,

Subin Hao

et al.

Green Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Jan. 1, 2024

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

Language: Английский

Citations

2
Electrochemically Benzyl Cation‐Triggered Alkylacetoxylation of Terminal Alkynes and Carboxylic Acids DOI
Na Yang, Hui Gao,

Peng‐Zhan Zhang

et al.

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(12), P. 2721 - 2727

Published: May 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.

Language: Английский

Citations

1
Electrochemical N‐Centered Radical‐Triggered Intramolecular N‐N Coupling for the Cyclization of o‐Aminyl Azobenzenes DOI Open Access

Anna Gao,

K. K. N. CHEN,

Fang Ma

et al.

European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 27(46)

Published: Aug. 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.

Language: Английский

Citations

1
Photo- and Electro-chemical Strategies for Indazole Synthesis DOI Creative Commons
Binbin Huang

Tetrahedron Chem, Journal Year: 2024, Volume and Issue: unknown, P. 100116 - 100116

Published: Dec. 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.

Language: Английский

Citations

1