Regioselective Monoarylation of 2-Phenylbenzimidazole via Ruthenium-Catalyzed­ C–H Bond Functionalization

Kobayashi, Yasuyuki; Kashiwa, Mitsuhiro; Sonoda, Motohiro; Kirihata, Mitsunori; Tanimori, Shinji

doi:10.1055/s-0034-1379013

Cited by 14 publications

References 6 publications

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Ruthenium‐Catalyzedortho‐CH Bond Arylation Reactions

Bruneau¹,

Gramage‐Doria²

2022

Handbook of CH-Functionalization

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The highly selective ruthenium-catalyzed ortho-C-H bond arylations have met a level of maturity that makes them an attractive tool to achieve unique organic transformations.By means of the manifold mechanisms operating in the presence of different arylating agents and reaction conditions, these methodologies have succeeded in reducing the wastes/steps towards the desired molecules as well as enlarging the chemical space by affording molecules impossible to obtain otherwise. The key achievements in this area are discussed in this chapter. Introduction.Biaryl and terphenyl cores are widespread structures in many biologically active substances and have useful physical properties in material sciences. The seminal results on the synthesis of biphenyl by connecting two aryl iodide molecules via reductive coupling in the presence of copper were reported in 1901 [1] and this concept was further developed [2,3]. Since this discovery, continuous efforts have been devoted to the improvement of these aryl-aryl couplings, mainly based on palladium-catalyzed cross-coupling reactions of aryl (pseudo)halides with organometallic reagents leading to the formation of a new C(sp 2 )-C(sp 2 ) bonds (Figure 1a) [4][5][6][7][8].

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Ruthenium‐Catalyzedortho‐CH Bond Arylation Reactions

Bruneau¹,

Gramage‐Doria²

2022

Handbook of CH-Functionalization

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Exploration of C‐H Activation Strategies in Construction of Functionalized 2‐Aryl Benzoazoles: A Decisive Review

2021

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Transition metal‐catalyzed C−H bond activation has proved to be a powerful weapon for the synthesis and functionalization of privileged class of heterocycles. The 2‐aryl benzoazole (benzothiazoles, benzoxazoles and benzimidazoles) derivatives have surfaced in the scientific community with their potential applications in medicinal chemistry, agrochemistry and material science. The contribution of C−H activation strategies towards the functionalization of relevant 2‐aryl benzoazoles has been amenable in the drug discovery process. This review envelopes a decade account of the C−H activation strategies adopted for the functionalization of 2‐aryl benzoazoles.

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Reactivity of 4‐phenylthiazoles in ruthenium catalyzed direct arylations

Daher

Jacquemin

Guerchais

et al. 2019

Applied Organom Chemis

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The reactivity of the phenyl substituent of 4‐phenylthiazoles in Ru‐catalyzed direct arylation was studied. 4‐Phenylthiazole was found to be unreactive; whereas, the introduction of an aryl unit at C5‐position of 4‐phenylthiazole enhances its reactivity, allowing the selective mono‐arylation of the phenyl unit of 4‐phenylthiazoles in moderate to high yields using 5 mol% of [Ru(p‐cymene)Cl2]2 catalyst precursor associated to KOPiv as base. These results reveal that the conformation and electronic properties of 4‐phenylthiazoles are crucial to allow the formation of suitable intermediates in the course of the catalytic cycle. The reaction tolerated both electron‐rich and electron‐poor aryl bromides allowing the straightforward tuning of the electronic properties of the arylated 2‐methyl‐4‐phenyl‐5‐arylthiazoles.

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Regioselective Monoarylation of 2-Phenylbenzimidazole via Ruthenium-Catalyzed C–H Bond Functionalization

Cited by 14 publications

References 6 publications

Ruthenium‐Catalyzedortho‐CH Bond Arylation Reactions

Ruthenium‐Catalyzedortho‐CH Bond Arylation Reactions

Exploration of C‐H Activation Strategies in Construction of Functionalized 2‐Aryl Benzoazoles: A Decisive Review

Reactivity of 4‐phenylthiazoles in ruthenium catalyzed direct arylations

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Regioselective Monoarylation of 2-Phenylbenzimidazole via Ruthenium-Catalyzed­ C–H Bond Functionalization

Cited by 14 publications

References 6 publications

Ruthenium‐Catalyzedortho‐CH Bond Arylation Reactions

Ruthenium‐Catalyzedortho‐CH Bond Arylation Reactions

Exploration of C‐H Activation Strategies in Construction of Functionalized 2‐Aryl Benzoazoles: A Decisive Review

Reactivity of 4‐phenylthiazoles in ruthenium catalyzed direct arylations

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Regioselective Monoarylation of 2-Phenylbenzimidazole via Ruthenium-Catalyzed C–H Bond Functionalization