A covalent organic framework-catalyzed visible-light-induced three-component cascade synthesis of trifluoroalkyl and trifluoroalkenyl quinoxalin-2(1H)-one derivatives

Review Chemistry, Medicinal

Quinoxaline: A Chemical Moiety with Spectrum of Interesting Biological Activities

Aastha Sharma et al.

Summary: Quinoxaline is a nitrogenous heterocyclic moiety with a wide range of biological activities and potential medicinal applications, including antibacterial and anticancer properties.

MINI-REVIEWS IN MEDICINAL CHEMISTRY (2022)

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Article Chemistry, Organic

Visible-light induced C3-H trifluoromethylation of quinoxalin-2(1H)-ones with CF3SO2Cl under external photocatalyst-free conditions

Xia Mi et al.

Summary: A visible light-induced C-H trifluoromethylation of quinoxalin-2(1H)-ones using CF3SO2Cl as the CF3 radical source under photocatalyst-free conditions is reported in this study. The reaction proceeds smoothly through a radical process in the absence of photocatalyst and oxidant, offering an efficient and green method for the synthesis of 3-trifluoromethyl quinoxalin-2(1H)-ones.

TETRAHEDRON LETTERS (2022)

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Article Chemistry, Physical

Persistent radical cation sp2 carbon-covalent organic framework for photocatalytic oxidative organic transformations

Yuan-Zhe Cheng et al.

Summary: Persistent radical covalent organic frameworks (COFs) have shown great potential in photocatalysis, magnetism, and biology. We successfully synthesized two sp2 carbon-covalent organic frameworks with persistent triphenylamine radical cation, which can be generated by simple light irradiation. These materials can be used for oxidative organic transformations under visible light.

APPLIED CATALYSIS B-ENVIRONMENTAL (2022)

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Article Chemistry, Physical

Facile synthesis of 2D covalent organic frameworks for cooperative photocatalysis with TEMPO: The selective aerobic oxidation of benzyl amines

Xia Li et al.

Summary: 2D covalent organic frameworks (COFs) have recently shown promise as versatile photoactive functional materials. In this study, three 8-ketoenamine linked 2D COFs were successfully assembled, with Tp-BTD-25 exhibiting superior activity for photocatalytic oxidation reactions at lower temperature. The addition of TEMPO enhanced both stability and activity of the photocatalyst.

APPLIED CATALYSIS B-ENVIRONMENTAL (2022)

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Article Chemistry, Multidisciplinary

Dual Metalation in a Two-Dimensional Covalent Organic Framework for Photocatalytic C-N Cross-Coupling Reactions

Ayan Jati et al.

Summary: This study presents a dual metalation strategy using a COF TpBpy for C-N cross-coupling reactions. The strategy demonstrates controlled metalation, recyclability, and visible-light-mediated catalysis. Experimental and theoretical studies provide insights into the catalyst and reaction mechanism.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2022)

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Article Chemistry, Organic

Photoinduced Three-Component Difluoroalkylation of Quinoxalinones with Alkenes via Difluoroiodane(III) Reagents

Ningning Zhou et al.

Summary: An environmentally friendly strategy for a photo- catalyzed three-component reaction between quinoxalinones, alkenes, and hypervalent iodine(III) reagents is disclosed. The designed difluoroiodane(III) reagent shows excellent reactivity and can provide a wide range of difluoroalkyl-substituted quinoxaline-2(1H)-ones in moderate to excellent yields under mild conditions. Experimental studies confirm the involvement of a difluoroalkyl radical intermediate in the reaction.

ORGANIC LETTERS (2022)

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Article Chemistry, Physical

A cobalt covalent organic framework: a dual-functional atomic-level catalyst for visible-light-driven C-H annulation of amides with alkynes

Jingwen Jia et al.

Summary: The merger of transition-metal catalysis and photoredox catalysis has achieved a balance between chemical transformation and the rational use of light energy. A dual-functional cobalt covalent organic framework (CoCOF-SYNU-1) was synthesized for visible-light-driven C-H annulation of amides with alkynes. The reaction showed excellent catalyst recyclability and practicability.

JOURNAL OF MATERIALS CHEMISTRY A (2022)

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Article Chemistry, Organic

C-H benzylation of quinoxalin-2(1H)-ones via visible-light riboflavin photocatalysis

Qiuli Yan et al.

Summary: A highly efficient visible-light promoted benzylation method using riboflavin as a green photocatalyst has been developed for synthesizing C3-benzylated quinoxalin-2(1H)-one derivatives. This method offers a new approach for the synthesis of these derivatives, with potential applications in pharmaceutical and synthetic chemistry.

ORGANIC CHEMISTRY FRONTIERS (2022)

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Article Chemistry, Multidisciplinary

Visible-light-induced three-component reaction of quinoxalin-2(1H)-ones, alkenes and CF3SO2Na leading to 3-trifluoroalkylated quinoxalin-2(1H)-ones

Na Meng et al.

Summary: A metal-free visible-light-enabled three-component reaction has been developed, which utilizes quinoxalin-2(1H)-ones, alkenes, and CF3SO2Na under air at room temperature. This photocatalytic tandem reaction using 4CzIPN as the photocatalyst and air as the green oxidant provides a mild and environmentally friendly approach to access a series of 3-trifluoroalkylated quinoxalin-2(1H)-ones.

CHINESE CHEMICAL LETTERS (2021)

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Article Chemistry, Multidisciplinary

A Visible-Light-Harvesting Covalent Organic Framework Bearing Single Nickel Sites as a Highly Efficient Sulfur-Carbon Cross-Coupling Dual Catalyst

Hui Chen et al.

Summary: This study explores a new COF material that combines photosensitivity and nickel catalytic activity to form a dual-functional catalyst. The catalyst shows excellent catalytic performance in the visible-light-driven catalytic sulfur-carbon cross-coupling reaction. This research demonstrates for the first time the use of a photosensitive COF scaffold and single transition metal sites as a two-component synergistic catalyst in organic transformation.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

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Article Chemistry, Multidisciplinary

Metal-, Photocatalyst-, Light- and Electrochemical-Free C-3 Trifluoromethylation of Quinoxalin-2(1H)-ones, Imidazo[1,2-a]pyridines and 2H-Indazoles

Nibedita Baruah Dutta et al.

Summary: An efficient protocol for the synthesis of various trifluoromethylated compounds under metal-, photocatalyst-, light- and electrochemical-free conditions was reported. This protocol involves the use of Langlois' reagent in combination with an oxidant to promote the free radical trifluoromethylation reaction, resulting in high yields. Radical scavenging experiments confirmed the involvement of radicals in the reaction.

CHEMISTRYSELECT (2021)

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Article Chemistry, Physical

Photoredox Heterobimetallic Dual Catalysis Using Engineered Covalent Organic Frameworks

Alberto Lopez-Magano et al.

Summary: The functionalization of an imine-based layered covalent organic framework has allowed the obtention of a heterobimetallated material with photoactive Ir and Ni fragments immobilized within the porous structure. These heterogeneous light-mediated reactions showed enhanced activity and stability compared to analogous homogeneous systems.

ACS CATALYSIS (2021)

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Article Chemistry, Multidisciplinary

Graphene oxide-catalyzed trifluoromethylation of alkynes with quinoxalinones and Langlois' reagent

Hong Li et al.

Summary: The direct C-H trifluoromethylation of alkynes and quinoxalinones has been achieved using a graphene oxide/Langlois' reagent system, resulting in the formation of olefinic C-CF3 to access a series of 3-trifluoroalkylated quinoxalin-2(1H)-ones.

RSC ADVANCES (2021)

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Article Chemistry, Organic

Photoredox-catalyzed 2,2,2-trifluoroethylation and 2,2-difluoroethylation of alkenes with concomitant introduction of a quinoxalin-2(1H)-one moiety

Xiu Yang et al.

Summary: This research has developed a new strategy using photoredox-palladium catalysis for the difunctionalization of alkenes with readily available quinoxalin-2(1H)-ones and inexpensive ICH2CF3/ICH2CF2H, providing the corresponding three-component coupling products in moderate to high yields and excellent regioselectivity, which offers a new protocol to access valuable CF3CH2- and HCF2CH2-containing compounds.

ORGANIC CHEMISTRY FRONTIERS (2021)

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Review Chemistry, Multidisciplinary

Transition metal-free C-3 functionalization of quinoxalin-2(1H)-ones: recent advances and sanguine future

Kiran et al.

Summary: Transition metal-free C-3 functionalization of quinoxalin-2(1H)-ones has emerged as a modern sustainable protocol with robust applications in medicinal, pharmaceutical, and agricultural industries. Recent developments have focused on sustainable protocols for constructing C-C, C-N, C-P, C-S, and C-O bonds through C-H functionalization of these compounds. The shift towards metal-free methodologies in organic chemistry offers environmentally benign synthetic routes.

NEW JOURNAL OF CHEMISTRY (2021)

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Review Chemistry, Applied

Photo-/electrocatalytic functionalization of quinoxalin-2(1H)-ones

Kai Sun et al.

Summary: The review provides an overview of recent advances in the photo-/electrocatalytic functionalization of quinoxalin-2(1H)-ones, covering a variety of reactions and discussing the reaction scope and mechanism in detail.

CHINESE JOURNAL OF CATALYSIS (2021)

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Article Chemistry, Multidisciplinary

A highly stable all-in-one photocatalyst for aryl etherification: the NiII embedded covalent organic framework

Wenbo Dong et al.

Summary: The newly designed dual nickel/photocatalysis 2D covalent organic framework (COF) has successfully overcome the difficulties of recycling photosensitizers or nickel complexes, efficiently converting aryl bromides to aryl alkyl ethers with good substrate compatibility and functional group tolerance.

GREEN CHEMISTRY (2021)

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Article Chemistry, Multidisciplinary

Covalent Organic Frameworks: A Sustainable Photocatalyst toward Visible-Light-Accelerated C3 Arylation and Alkylation of Quinoxalin-2(1H)-ones

Miao Tian et al.

CHEMISTRY-A EUROPEAN JOURNAL (2020)

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Article Nanoscience & Nanotechnology

Structural Engineering of Two-Dimensional Covalent Organic Frameworks for Visible-Light-Driven Organic Transformations

Haoran Liu et al.

ACS APPLIED MATERIALS & INTERFACES (2020)

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Review Chemistry, Physical

Covalent organic frameworks for photocatalytic applications

Qing Yang et al.

APPLIED CATALYSIS B-ENVIRONMENTAL (2020)

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Review Chemistry, Organic

Recent advances and perspectives on the synthesis and C-H bond functionalization of quinoxalin-2(1H)-one

Prasanjit Ghosh et al.

SYNTHETIC COMMUNICATIONS (2020)

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Article Chemistry, Organic

Transition-metal-free, three-component trifluoromethylative heteroarylation of unactivated alkenes: Efficient access to β-trifluoromethylated quinoxalinones and preliminary antifungal evaluation against Magnaporthe grisea

Zhuoxian Shao et al.

TETRAHEDRON (2020)

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Article Chemistry, Organic

Metal-Free Trifluoroalkylation of Quinoxalin-2(1H)-ones with Unactivated Alkenes and Langlois' Reagent

Na Meng et al.

JOURNAL OF ORGANIC CHEMISTRY (2020)

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Review Chemistry, Applied

Fluorination and Fluoroalkylation Reactions Mediated by Hypervalent Iodine Reagents

Zhou-Zhou Han et al.

ADVANCED SYNTHESIS & CATALYSIS (2020)

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Article Chemistry, Physical

Triazine functionalized fully conjugated covalent organic framework for efficient photocatalysis

Yongliang Yang et al.

APPLIED CATALYSIS B-ENVIRONMENTAL (2020)

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Review Chemistry, Multidisciplinary

The C3-H Bond Functionalization of Quinoxalin-2(1H)-Ones With Hypervalent Iodine(III) Reagents

Yushi Tan et al.

FRONTIERS IN CHEMISTRY (2020)

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Article Chemistry, Multidisciplinary

Vinylene-Bridged Two-Dimensional Covalent Organic Frameworks via Knoevenagel Condensation of Tricyanomesitylene

Shuai Bi et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2020)

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Article Chemistry, Physical

Fully Conjugated Donor-Acceptor Covalent Organic Frameworks for Photocatalytic Oxidative Amine Coupling and Thioamide Cyclization

Shuai Li et al.

ACS CATALYSIS (2020)

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Article Chemistry, Medicinal

Substitution Effect of the Trifluoromethyl Group on the Bioactivity in Medicinal Chemistry: Statistical Analysis and Energy Calculations

Amina Abula et al.

JOURNAL OF CHEMICAL INFORMATION AND MODELING (2020)

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A hydrophilic covalent organic framework for photocatalytic oxidation of benzylamine in water

Ziqian Liu et al.

CHEMICAL COMMUNICATIONS (2020)

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Covalent organic frameworks: emerging high-performance platforms for efficient photocatalytic applications

Guang-Bo Wang et al.

JOURNAL OF MATERIALS CHEMISTRY A (2020)

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Covalent organic framework photocatalysts: structures and applications

Han Wang et al.

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Programming Covalent Organic Frameworks for Photocatalysis: Investigation of Chemical and Structural Variations

Sai Wang et al.

MATTER (2020)

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Design and applications of three dimensional covalent organic frameworks

Xinyu Guan et al.

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Rational synthesis of interpenetrated 3D covalent organic frameworks for asymmetric photocatalysis

Xing Kang et al.

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Designed Synthesis of a 2D Porphyrin-Based sp2 Carbon-Conjugated Covalent Organic Framework for Heterogeneous Photocatalysis

Rufan Chen et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019)

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Covalent organic framework as an efficient, metal-free, heterogeneous photocatalyst for organic transformations under visible light

Ziping Li et al.

APPLIED CATALYSIS B-ENVIRONMENTAL (2019)

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Triazine Functionalized Porous Covalent Organic Framework for Photo-organocatalytic E-Z Isomerization of Olefins

Mohitosh Bhadra et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2019)

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Visible-Light-Induced Trifluoromethylation of Quinoxalin-2(1H)-Ones under Photocatalyst-Free Conditions

Jiayang Wang et al.

ASIAN JOURNAL OF ORGANIC CHEMISTRY (2019)

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Photoinitiated Three-Component α-Perfluoroalkyl-β-heteroarylation of Unactivated Alkenes via Electron Catalysis

Danqing Zheng et al.

ORGANIC LETTERS (2019)

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Recent advances in the direct functionalization of quinoxalin-2(1H)-ones

Qiumin Ke et al.

ORGANIC & BIOMOLECULAR CHEMISTRY (2019)

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Visible-light-induced tandem radical addition-cyclization of 2-aryl phenyl isocyanides catalysed by recyclable covalent organic frameworks

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GREEN CHEMISTRY (2019)

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Covalent Organic Frameworks: Structures, Synthesis, and Applications

Maria S. Lohse et al.

ADVANCED FUNCTIONAL MATERIALS (2018)

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Asymmetric Covalent Triazine Framework for Enhanced Visible-Light Photoredox Catalysis via Energy Transfer Cascade

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ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2018)

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Benzoxazole-Linked Ultrastable Covalent Organic Frameworks for Photocatalysis

Pi-Feng Wei et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2018)

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Quinoxalinone as a Privileged Platform in Drug Development

Leilei Shi et al.

MINI-REVIEWS IN MEDICINAL CHEMISTRY (2018)

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Direct C-H Trifluoromethylation of Quinoxalin-2(1H)-ones under Transition-Metal-Free Conditions

Liping Wang et al.

ADVANCED SYNTHESIS & CATALYSIS (2018)

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Covalent organic frameworks as metal-free heterogeneous photocatalysts for organic transformations

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JOURNAL OF MATERIALS CHEMISTRY A (2017)

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Trifluoromethyl nitrogen heterocycles: synthetic aspects and potential biological targets

F. Meyer

CHEMICAL COMMUNICATIONS (2016)

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Design and Synthesis of Potent and Multifunctional Aldose Reductase Inhibitors Based on Quinoxalinones

Xiangyu Qin et al.

JOURNAL OF MEDICINAL CHEMISTRY (2015)

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Present status of quinoxaline motifs: Excellent pathfinders in therapeutic medicine

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EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY (2014)

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Shun Wan et al.

CHEMISTRY OF MATERIALS (2011)

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Quinoxalin-2(1H)-One Derivatives As Inhibitors Against Hepatitis C Virus

Rui Liu et al.

JOURNAL OF MEDICINAL CHEMISTRY (2011)

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NATURE (2011)

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The many roles for fluorine in medicinal chemistry

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SCIENCE (2005)

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A covalent organic framework-catalyzed visible-light-induced three-component cascade synthesis of trifluoroalkyl and trifluoroalkenyl quinoxalin-2(1H)-one derivatives

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