The C-3 Functionalization of 1H-Indazole through Suzuki–Miyaura Cross-Coupling Catalyzed by a Ferrocene-Based Divalent Palladium Complex Immobilized over Ionic Liquid, as Well as Theoretical Insights into the Reaction Mechanism DOI Creative Commons

Jinmeng Yu,

Aqun Zheng,

Lu Jin

и другие.

Applied Sciences, Год журнала: 2023, Номер 13(7), С. 4095 - 4095

Опубликована: Март 23, 2023

The C-3 functionalization of 1H-indazole could produce a lot highly valuable pharmaceutical precursors, which be used for the treatment cancer and many other inflammatory diseases. This work was focused on through Suzuki–Miyaura cross-coupling 3-iodo-1H-indazole with organoboronic acids, catalyzed by various palladium catalysts immobilized over imidazolium ionic liquids, as well catalyst recycling. A series reaction parameters, including substrate, catalyst, liquid, were fully investigated. It is significant to note that yields present mainly determined solvent used, more than chemical structure substrate. Furthermore, ferrocene-based divalent complexes showed better catalytic outputs compared simple salts. Moreover, using two BMImX (BMIm+ = 1-n-butyl-3-methylimidazolium, X− BF4−, PF6−) not only improved cross-coupled products, but also avoided formation Pd(0) black, non-ionic liquid facilitated reactions, simultaneously making recycling effective. On average, BMImBF4 performed BMImPF6. Additionally, scientific calculations revealed 1,1′-bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex (PdCl2(dppf)) lower energy barrier in intermediates [1,1′-bis(di-tert-butylphosphino)ferrocene]dichloropalladium(II) (PdCl2(dtbpf)), leading higher outputs. may contribute development 1H-indazole-derived new pharmaceuticals.

Язык: Английский

Visible light-induced organophotoredox-catalyzed difunctionalization of alkenes and alkynes DOI

Subham Gupta,

Abhishek Kundu, Sumit Ghosh

и другие.

Green Chemistry, Год журнала: 2023, Номер 25(21), С. 8459 - 8493

Опубликована: Янв. 1, 2023

This review comprehensively summarizes visible light-induced difunctionalization strategies for alkene and alkyne systems in metal-free conditions with literature coverage up to July 2023.

Язык: Английский

Процитировано

40

Visible-light-induced cascade reaction: a sustainable approach towards molecular complexity DOI
Sumit Ghosh, Pranjal Pyne,

Anogh Ghosh

и другие.

Organic & Biomolecular Chemistry, Год журнала: 2023, Номер 21(8), С. 1591 - 1628

Опубликована: Янв. 1, 2023

Photoredox catalysis has demonstrated rapid evolution in the field of synthetic organic chemistry. On other hand, splendour cascade reactions providing complex molecular architectures renders them a cutting-edge research area. Therefore, merging photocatalysis with synthesis brings out paradigm immense potential. The development photocascade for target molecule particular skeleton and stereochemical framework presents certain challenges but provides robust environmentally benign alternative. This comprehensive review assembles all accomplishments highlights visible-light-induced literature coverage up to October 2022.

Язык: Английский

Процитировано

30

Redox-neutral carbon–heteroatom bond formation under photoredox catalysis DOI
Sumit Ghosh, Souvik Majumder, Debashis Ghosh

и другие.

Chemical Communications, Год журнала: 2023, Номер 59(46), С. 7004 - 7027

Опубликована: Янв. 1, 2023

This feature article presents all the recent reports on photoredox-catalyzed redox-neutral carbon–heteroatom coupling reactions up to March 2023.

Язык: Английский

Процитировано

29

Visible-Light Photocatalyzed C3–H Alkylation of 2H-Indazoles/Indoles with Sulfoxonium Ylides via Diversified Mechanistic Pathways DOI
Altman Yuzhu Peng, Yujing Wang, Kaifeng Wang

и другие.

ACS Catalysis, Год журнала: 2024, Номер 14(2), С. 1193 - 1204

Опубликована: Янв. 9, 2024

Herein, the C3–H alkylation of 2H-indazoles and indoles with sulfoxonium ylides is developed under visible-light photocatalysis. This protocol employs easily accessible reagents, a wide range 2H-indazoles, indoles, are suitable for this reaction to afford desired products benign conditions. Synergistic experimental computational studies suggest that involving photocatalysis could proceed via different mechanistic pathways. For C3-alkylation triplet energy transfer pathway proposed quenching excited photocatalyst. Subsequently, formed state undergo radical attack on C═S moiety ylides. After dissociation DMSO 1,2-H migration, final product be yielded. However, such not applicable indoles. Instead, converted C-centered in presence KH2PO4 photoredox The can C3-site thus lead

Язык: Английский

Процитировано

13

Photochemical and Electrochemical Synthesis of Oxazoles and Isoxazoles: An Update DOI
Debashis Ghosh,

Ancy Sherin,

Sumit Ghosh

и другие.

Advanced Synthesis & Catalysis, Год журнала: 2024, Номер 366(10), С. 2186 - 2208

Опубликована: Апрель 4, 2024

Abstract This review presents an outline of current advancements in the photochemical and electrochemical synthesis oxazoles isoxazoles. Oxazole isoxazole are important building blocks for a variety medicinally useful compounds. Therefore, these heterocycles via sustainable technologies is worth demanding. Photochemical two among few technologies. covers brief discussion on reaction parameters like catalysts, substrates scope, temperature, solvents, electrodes, electrolytes (in case process), light source process) individual reaction. Detailed mechanistic insight each also presented. Finally, summary, future direction toward development effective methods isoxazoles

Язык: Английский

Процитировано

10

Properties, Synthesis, and Characterization of Cu-Based Nanomaterials DOI

M. Vandana,

Aman Sharma, Kiran Bijapur

и другие.

ACS symposium series, Год журнала: 2024, Номер unknown, С. 1 - 33

Опубликована: Май 14, 2024

Copper-based nanomaterials offer a fascinating array of properties that make them pivotal in various technological applications. These materials, when scaled down to the nanoscale, exhibit enhanced electrical conductivity, surpassing their bulk counterparts. This book chapter primarily focuses on properties, synthesis, and characterization copper nanoparticles while also discussing metal oxide nanoparticles. Their large surface-to-volume ratios enable efficient electron transport, making valuable components electronics conductive inks for flexible devices. Furthermore, possess exceptional thermal crucial heat management advanced interface materials. Copper have positive economic environmental effects. catalytic render important diverse chemical reactions as energy storage systems like batteries supercapacitors. Additionally, tunability optical makes suitable photonic optoelectronic applications, ranging from sensors light-emitting The multifaceted copper-based continue drive innovation across broad spectrum industries.

Язык: Английский

Процитировано

8

Electrochemically Enabled Dehydrogenative Phosphorothiolation of 2H‐Indazoles under Electrolyte‐Free Conditions DOI
Payel Ghosh, Alakananda Hajra

Advanced Synthesis & Catalysis, Год журнала: 2022, Номер 364(23), С. 4157 - 4165

Опубликована: Окт. 18, 2022

Abstract We have developed an electrochemical method for phosphorothiolation of 2 H ‐indazoles using S ‐hydrogen phosphorothioates via cross dehydrogenative coupling reaction under metal‐free and electrolyte‐free conditions. This protocol is compatible with electron donating groups like −Me, −OMe, halogen elctron withdrawing such as −COOEt, affording respective indazolyl in 62%‐91% yields. Comprehensive mechanistic studies indicate that the proceeds through a radical pathway. magnified image

Язык: Английский

Процитировано

26

Recent advances in C–H functionalization of 2H-indazoles DOI

Zixian Yang,

Jin‐Tao Yu, Changduo Pan

и другие.

Organic & Biomolecular Chemistry, Год журнала: 2022, Номер 20(39), С. 7746 - 7764

Опубликована: Янв. 1, 2022

2H-Indazoles are one class of the most important nitrogen-containing heterocyclic compounds. The 2H-indazole motif is widely present in bioactive natural products and drug molecules that exhibit distinctive bioactivities. Therefore, much attention has been paid to access diverse derivatives. Among them, late-stage functionalization 2H-indazoles via C-H activation recognized as an efficient approach for increasing complexity diversity In this review, we summarized recent achievements 2H-indazoles, including C3-functionalization through transition metal-catalyzed or a radical pathway, ortho C2'-H remote at benzene ring 2H-indazoles.

Язык: Английский

Процитировано

25

Recent advances in carbosilylation of alkenes and alkynes DOI

Prajna Paramita Pal,

Sumit Ghosh, Alakananda Hajra

и другие.

Organic & Biomolecular Chemistry, Год журнала: 2023, Номер 21(11), С. 2272 - 2294

Опубликована: Янв. 1, 2023

This review presents a collective discussion on recent accomplishments in carbosilylation of alkenes and alkynes up to January 2023.

Язык: Английский

Процитировано

15

Minisci‐Type Carbamoylation of Azauracils with Oxamic Acids DOI
Changduo Pan, Dongdong Chen,

Miao Zeng

и другие.

European Journal of Organic Chemistry, Год журнала: 2024, Номер 27(7)

Опубликована: Янв. 19, 2024

Abstract A Minisci‐type carbamoylation of azauracils was developed to afford 6‐carbamoyl in yields up 94 %. In this transformation, oxamic acids were employed as the carbamoyl radical sources under metal‐free conditions. It features high atom economy, good functional group compatibility and convenient operation.

Язык: Английский

Процитировано

5