Transition-Metal-Free C–H Arylation of Unactivated Arenes with 8-Hydroxyquinoline as a Promoter

Zheng, Xuehua; Wu, Xu-Nian; Chen, Jingyi; Luo, Hai‐Bin; Wu, Deyan; Wu, Yinuo

doi:10.1055/s-0036-1591874

Cited by 3 publications

(3 citation statements)

References 17 publications

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“…The latter is formed via a single-electron transfer to [CuLn] 2+• , regenerating the catalyst. The second catalytic cycle can alternatively proceed in the absence of a copper catalyst via a radical pathway promoted by K 2 CO 3 (base-promoted HAS). − …”

Section: Resultsmentioning

confidence: 99%

Microwave-Assisted, Copper-Catalyzed Domino O–H/C–H Arylation Reaction toward the Synthesis of Oxygen-Doped Polyaromatic Molecules

Kaplanai,

Tonis,

Drymona

et al. 2023

J. Org. Chem.

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Benzoxanthenes and their analogues are a very important class of compounds mainly due to their wide range of biological and technological applications. The development of a new methodology for their synthesis, involving an Ullmann-type coupling followed by an intramolecular C–H arylation, catalyzed by copper in a domino fashion, is reported. A variety of para-substituted phenols are amenable to this methodology, affording the desired products in moderate to good yields. Our protocol is expedient and practical and is carried out under microwave irradiation in only 3 min under air. A plausible catalytic cycle is proposed based on experimental mechanistic investigations and density functional theory (DFT) calculations.

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Section: Resultsmentioning

confidence: 99%

Microwave-Assisted, Copper-Catalyzed Domino O–H/C–H Arylation Reaction toward the Synthesis of Oxygen-Doped Polyaromatic Molecules

Kaplanai,

Tonis,

Drymona

et al. 2023

J. Org. Chem.

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“…Several reviews on whole cell redox biocatalysis have been published in recent years. [30][31][32] Here, we highlight recent progress in whole cell catalysis involving carbonyl reductases from microorganisms that have been used for scalable chemical production of chiral alcohols with a broad substrate scope.…”

Section: Anju Chadhamentioning

confidence: 99%

“…65 It is important to identify and develop various new biocatalytic routes that can be scaled up quickly. 30,66,67 The use of whole cells expressing recombinant enzymes would pave the way to improve the efficiency of enzymes involved in biocatalytic reactions, although it increases the cost of production.…”

Section: Organic and Biomolecular Chemistry Reviewmentioning

confidence: 99%

Microbial alcohol dehydrogenases: recent developments and applications in asymmetric synthesis

Chadha,

Padhi,

Stella

et al. 2024

Org. Biomol. Chem.

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[2,3‐Bis‐(2‐pyridyl) pyrazine] as an Efficient Organocatalyst for the Direct C_(sp²₎‐H Arylation of Unactivated Arenes/Heteroarenes via C−H Bond Activation

2020

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Herein, we report the identification of 2,3-bis-(2-pyridyl) pyrazine as a new organocatalyst, which has been utilized for the direct cross-coupling reactions of an aryl halide with unactivated arenes/heteroarenes via C (sp 2)-H bond activation. This transition metal-free CÀ H arylation of unactivated benzenes with aryl halides (ArÀ X; X=I, Br, Cl) underwent smoothly with only 10 mol% of an organocatalyst and in the presence of 3 equivalent of potassium tert-butoxide base which furnished a library of biaryls (3 a-u) in up to 98 % excellent yield under milder reaction conditions. The mechanistic pathway involves the in-situ formation of aryl radical anion intermediate and progressed via a single electron transfer (SET) mechanism. The wide substrate scope, high functional group forbearance, control/competition experiments, gram-scale synthesis and kinetic studies signify the prominence and useful nature of the protocol along with the steadiness of the novel organocatalyst.

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Transition-Metal-Free C–H Arylation of Unactivated Arenes with 8-Hydroxyquinoline as a Promoter

Cited by 3 publications

References 17 publications

Microwave-Assisted, Copper-Catalyzed Domino O–H/C–H Arylation Reaction toward the Synthesis of Oxygen-Doped Polyaromatic Molecules

Microwave-Assisted, Copper-Catalyzed Domino O–H/C–H Arylation Reaction toward the Synthesis of Oxygen-Doped Polyaromatic Molecules

Microbial alcohol dehydrogenases: recent developments and applications in asymmetric synthesis

[2,3‐Bis‐(2‐pyridyl) pyrazine] as an Efficient Organocatalyst for the Direct C_(sp²₎‐H Arylation of Unactivated Arenes/Heteroarenes via C−H Bond Activation

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Transition-Metal-Free C–H Arylation of Unactivated Arenes with 8-Hydroxyquinoline as a Promoter

Cited by 3 publications

References 17 publications

Microwave-Assisted, Copper-Catalyzed Domino O–H/C–H Arylation Reaction toward the Synthesis of Oxygen-Doped Polyaromatic Molecules

Microwave-Assisted, Copper-Catalyzed Domino O–H/C–H Arylation Reaction toward the Synthesis of Oxygen-Doped Polyaromatic Molecules

Microbial alcohol dehydrogenases: recent developments and applications in asymmetric synthesis

[2,3‐Bis‐(2‐pyridyl) pyrazine] as an Efficient Organocatalyst for the Direct C(sp2)‐H Arylation of Unactivated Arenes/Heteroarenes via C−H Bond Activation

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[2,3‐Bis‐(2‐pyridyl) pyrazine] as an Efficient Organocatalyst for the Direct C_(sp²₎‐H Arylation of Unactivated Arenes/Heteroarenes via C−H Bond Activation