Reaction of Cycloalkene‐1‐carboxamides with Aryl Boronates via Rhodium(III)‐Catalyzed C−H Activation: A Versatile Route to 3,4‐Cycloalkaquinolin‐2(1<i>H</i>)‐ones

Zhu, You‐Quan; Hui, Li‐Wen; Niu, Yun‐Xia; Lv, Lin‐Ge; Zhu, Kun

doi:10.1002/adsc.201901047

Cited by 5 publications

(3 citation statements)

References 24 publications

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“…The Zhu group was able to construct the same scaffolds through an efficient Cp*Rh(III)-catalyzed alkenyl C−H functionalization of N-methoxycycloalkene carboxamides with aryl boronic acid pinacol esters (Scheme 204). 347 Even though asymmetric C−H activation is extremely useful for obtaining chiral compounds, controlling their stereochemistry is an extremely difficult task in some cases. 348−352 Enantioselective C−H functionalization often demands harsh reaction conditions and high temperature that are incompatible with many asymmetric reactions.…”

Section: 37mentioning

confidence: 99%

“…The Zhu group was able to construct the same scaffolds through an efficient Cp*Rh(III)-catalyzed alkenyl C–H functionalization of N -methoxycycloalkene carboxamides with aryl boronic acid pinacol esters (Scheme ). A variety of N -methoxycycloalkene carboxamide derivatives reacted smoothly with diverse aryl boronates in the presence of 5 mol % [RhCp*Cl 2 ] 2 catalyst and 2 equiv of Ag 2 O oxidant to furnish the corresponding cycloalkaquinolinones in up to 92% yield. On the basis of detailed mechanistic investigations, the authors revealed that this annulative transformation may occur via a dual C–H activation pathway.…”

Section: Alkenyl C–h Bond Functionalization Of Alkenes Containing An ...mentioning

confidence: 99%

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Recent Advances in Alkenyl sp² C–H and C–F Bond Functionalizations: Scope, Mechanism, and Applications

et al. 2022

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Alkenes and their derivatives are featured widely in a variety of natural products, pharmaceuticals, and advanced materials. Significant efforts have been made toward the development of new and practical methods to access this important class of compounds by selectively activating the alkenyl C(sp2)–H bonds in recent years. In this comprehensive review, we describe the state-of-the-art strategies for the direct functionalization of alkenyl sp2 C–H and C–F bonds until June 2022. Moreover, metal-free, photoredox, and electrochemical strategies are also covered. For clarity, this review has been divided into two parts; the first part focuses on currently available alkenyl sp2 C–H functionalization methods using different alkene derivatives as the starting materials, and the second part describes the alkenyl sp2 C–F bond functionalization using easily accessible gem-difluoroalkenes as the starting material. This review includes the scope, limitations, mechanistic studies, stereoselective control (using directing groups as well as metal-migration strategies), and their applications to complex molecule synthesis where appropriate. Overall, this comprehensive review aims to document the considerable advancements, current status, and emerging work by critically summarizing the contributions of researchers working in this fascinating area and is expected to stimulate novel, innovative, and broadly applicable strategies for alkenyl sp2 C–H and C–F bond functionalizations in the coming years.

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Section: 37mentioning

confidence: 99%

Section: Alkenyl C–h Bond Functionalization Of Alkenes Containing An ...mentioning

confidence: 99%

Recent Advances in Alkenyl sp² C–H and C–F Bond Functionalizations: Scope, Mechanism, and Applications

et al. 2022

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“…In 2019, Zhu reported a Rh-catalyzed, amide-directed, double C–H bond activation strategy to prepare cycloalkaquinolones 66 with arylboronic acid 64 pinacol esters 65 ( Scheme 18 ) [ 102 ]. The products were obtained in moderate to excellent yields and showed broad scope and high functional group tolerance.…”

Section: Two-component Reactionsmentioning

confidence: 99%

Recent Advances in One-Pot Modular Synthesis of 2-Quinolones

2020

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It is known that 2-quinolones are broadly applicable chemical structures in medicinal and agrochemical research as well as various functional materials. A number of current publications about their synthesis and their applications emphasize the importance of these small molecules. The early synthetic chemistry originated from the same principle of the classical Friedländer and Knorr procedures for the preparation of quinolines. The analogous processes were developed by applying new synthetic tools such as novel catalysts, the microwave irradiation method, etc., whereas recent innovations in new bond forming reactions have allowed for novel strategies to construct the core structures of 2-quinolones beyond the bond disconnections based on two classical reactions. Over the last few decades, some reviews on structure-based, catalyst-based, and bioactivity-based studies have been released. In this focused review, we extensively surveyed recent examples of one-pot reactions, particularly in view of modular approaches. Thus, the contents are categorized as three major sections (two-, three-, and four-component reactions) according to the number of reagents that ultimately compose atoms of the core structures of 2-quinolones. The collected synthetic methods are discussed from the perspectives of strategy, efficiency, selectivity, and reaction mechanism.

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Organocatalytic Electrophilic Arene Amination: Rapid Synthesis of 2‐Quinolones

Das,

Ghosh,

Grimm

et al. 2024

Chemistry A European J

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For decades, the synthesis of 2‐quinolones, a crucial structural motif in pharmaceuticals and agrochemicals, has relied heavily on costly noble metal complexes and structurally complex ligands. Despite considerable efforts from synthetic chemists, a mild, metal‐free, environmentally friendly, and cost‐effective approach has remained elusive. This study introduces a robust, metal‐free synthetic platform that leverages an innovative organoiodine‐catalyzed electrophilic arene C(sp2)‐H amination strategy to efficiently produce a wide range of new and modifiable 2‐quinolones. Moreover, this study allows ready synthetic access to novel 8‐aryl‐substituted 2‐quinolones, uncovering new chemical spaces with significant potential for medicinal applications.

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Reaction of Cycloalkene‐1‐carboxamides with Aryl Boronates via Rhodium(III)‐Catalyzed C−H Activation: A Versatile Route to 3,4‐Cycloalkaquinolin‐2(1H)‐ones

Cited by 5 publications

References 24 publications

Recent Advances in Alkenyl sp² C–H and C–F Bond Functionalizations: Scope, Mechanism, and Applications

Recent Advances in Alkenyl sp² C–H and C–F Bond Functionalizations: Scope, Mechanism, and Applications

Recent Advances in One-Pot Modular Synthesis of 2-Quinolones

Organocatalytic Electrophilic Arene Amination: Rapid Synthesis of 2‐Quinolones

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Reaction of Cycloalkene‐1‐carboxamides with Aryl Boronates via Rhodium(III)‐Catalyzed C−H Activation: A Versatile Route to 3,4‐Cycloalkaquinolin‐2(1H)‐ones

Cited by 5 publications

References 24 publications

Recent Advances in Alkenyl sp2 C–H and C–F Bond Functionalizations: Scope, Mechanism, and Applications

Recent Advances in Alkenyl sp2 C–H and C–F Bond Functionalizations: Scope, Mechanism, and Applications

Recent Advances in One-Pot Modular Synthesis of 2-Quinolones

Organocatalytic Electrophilic Arene Amination: Rapid Synthesis of 2‐Quinolones

Contact Info

Product

Resources

About

Recent Advances in Alkenyl sp² C–H and C–F Bond Functionalizations: Scope, Mechanism, and Applications

Recent Advances in Alkenyl sp² C–H and C–F Bond Functionalizations: Scope, Mechanism, and Applications