Small organic molecules with tailored structures: initiators in the transition-metal-free C–H arylation of unactivated arenes

Liu, Zhenghui; Wang, Peng; Chen, Yu; Yan, Zhenzhong; Chen, Suqing; Mu, Tiancheng

doi:10.1039/d0ra01845g

Cited by 12 publications

(9 citation statements)

References 70 publications

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“…The radical mechanism for biaryl formation via cross-coupling of arenes with aryl halides under different conditions has been proposed in several literature studies. , In the present work, a radical mechanism is also proposed on the basis of the control experiments and the computational studies.…”

Section: Resultsmentioning

confidence: 91%

“…In the past 2 decades, under transition-metal-free conditions, efficient procedures for biaryl syntheses from cross-coupling reactions of arene and aryl halides promoted by bases have also been developed . As shown in Scheme , with the use of different ligands, the alkali salts of KO t Bu, NaO t Bu, and NaH have been found to be efficient promoters or catalysts for this transformation …”

Section: Introductionmentioning

confidence: 99%

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Biaryl Formation via Base-Promoted Direct Coupling Reactions of Arenes with Aryl Halides

Iqbal

Mehmood

et al. 2021

ACS Omega

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In the absence of ligand, Cs 2 CO 3 -promoted cross-coupling reaction of arenes with cyano-/nitro-substituted aryl halides in DMSO affording biaryls is reported. The cyano/nitro group in biaryls is useful and convenient for further transformation. The formation of dibenzofurans resulting from the reactions between arenes and 1-bromo-2-iodobenzene is also reported. On the basis of control experiments and theoretical studies, a radical mechanism is proposed for the formation of biaryls.

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Section: Resultsmentioning

confidence: 91%

Section: Introductionmentioning

confidence: 99%

Biaryl Formation via Base-Promoted Direct Coupling Reactions of Arenes with Aryl Halides

Iqbal

Mehmood

et al. 2021

ACS Omega

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“…The authors have cited additional references within the Supporting Information. [31][32][33][34][35][36][37][38][39][40][41][42]…”

Section: Supporting Informationmentioning

confidence: 99%

Multielectron Redox Afforded by a Pincer Ligand Promoting Kumada Cross‐Coupling Reactions

Singh,

Jain,

Nath

et al. 2023

Chemistry A European J

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The redox‐active nature of a pincer has been exploited to conduct C−C cross‐coupling reactions under mild conditions. A nickel complex with a NNN pincer was dimeric in the solid state, and the structure displayed a Ni2N2 diamond core. In the dimeric structure, both ligand backbones house an electron, in the iminosemiquinonate form, to keep the metal's oxidation state at +2. In the presence of an aryl Grignard reagent, only 3 mol % loading the nickel complex generates a Kumada cross‐coupled product in good yield from a wide variety of aryl‐X (X= I, Br, Cl) substrates. That the ligand‐based radical remains responsible for promoting such a coupling reaction following a radical pathway is suggested by TEMPO quenching. Furthermore, a radical‐clock experiment along with tracing product distribution unambiguously supported the radical's involvement through the catalytic cycle. A series of thorough mechanistic probation, including computational DFT analysis, disclosed the cooperative action of both redox‐active pincer ligand and the metal centre to drive the reaction.

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“…It was reported that the t-BuOK-promoted arylation of iodo thiophenes and iodo pyridines with benzene can be catalyzed by simple organic molecules containing heteroatoms such as nitrogen and oxygen (Scheme 3). 11 Scheme 3 Tailored structure-mediated arylation of iodo heteroarenes A method was reported for the intramolecular arylation of N-(2-iodobenzyl)indoles bearing 1,10-phenanthroline, potassium tert-butoxide, and chlorobenzene (Scheme 4). 12 The method served to synthesize various 6H-isoindolo[2,1-a]-indole derivatives in high yields.…”

Section: Scheme 2 Incl3-catalyzed Arylation Of π-Deficient Heterocycles With 1hindolesmentioning

confidence: 99%

Section: Scheme 2 Incl 3 -Catalyzed Arylation Of -Deficient Heterocycles With 1h-indolesmentioning

confidence: 99%

Recent Advances in the Transition-Metal-Free Arylation of Heteroarenes

Uçar¹,

Daştan²

2021

Synthesis

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Transition-metal-free arylation reactions have attracted considerable attention, because of economic and environmental reasons over the past 40 years. In recent years, in particular, many efforts have been made to develop efficient transition-metal-free approaches for the arylation of heteroarenes. Covering the literature from 2015 to early 2021, this review aims to provide a comprehensive overview of the synthetic and mechanistic aspects of these atom economical and environmentally harmless reactions. 1 Introduction 2 Arylation of Pre-functionalized Heteroarenes 3 Direct C-H Arylation of Heteroarenes 3.1 C(Sp2)-H Arylation 3.2 C(sp3)-H Arylation 4 N-Arylation of Heteroarenes 5 Summary and Outlook

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Small organic molecules with tailored structures: initiators in the transition-metal-free C–H arylation of unactivated arenes

Abstract: A small organic molecule was tailored for the efficient synthesis of biphenyl and its derivatives from aryl iodides.

Cited by 12 publications

References 70 publications

Biaryl Formation via Base-Promoted Direct Coupling Reactions of Arenes with Aryl Halides

Biaryl Formation via Base-Promoted Direct Coupling Reactions of Arenes with Aryl Halides

Multielectron Redox Afforded by a Pincer Ligand Promoting Kumada Cross‐Coupling Reactions

Recent Advances in the Transition-Metal-Free Arylation of Heteroarenes

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Small organic molecules with tailored structures: initiators in the transition-metal-free C–H arylation of unactivated arenes

Abstract: A small organic molecule was tailored for the efficient synthesis of biphenyl and its derivatives from aryl iodides.

Cited by 12 publications

References 70 publications

Biaryl Formation via Base-Promoted Direct Coupling Reactions of Arenes with Aryl Halides

Biaryl Formation via Base-Promoted Direct Coupling Reactions of Arenes with Aryl Halides

Multielectron Redox Afforded by a Pincer Ligand Promoting Kumada Cross‐Coupling Reactions

Recent Advances in the Transition-Metal-Free Arylation of Hetero­arenes

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Recent Advances in the Transition-Metal-Free Arylation of Heteroarenes