Synthesis of 2-Benzoylbenzofurans <i>via</i> Palladium(II)-catalyzed Cascade Reactions

Luo, Haofan; Wang, Zijuan; Chen, Wenteng; He, Chang; Zhang, Guolin

doi:10.1080/00304948.2020.1862636

Cited by 3 publications

(5 citation statements)

References 20 publications

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“…Based on the results and our previous work, [21][22][23][24] In summary, we have discovered an efficient, palladiumcatalyzed approach for unsymmetrical 2,6-disubstituted pyrazines. This strategy underwent well with an acceptable tolerance on substrate scope in good to excellent yields.…”

Section: Synthesismentioning

confidence: 64%

“…Based on the results and our previous work, [21][22][23][24] a tentative mechanism for the construction of unsymmetrical 2,6disubstituted pyrazines is proposed in Scheme 2. Initially, Pd(OAc) 2 coordinates with the ligand and generates A.…”

Section: Paper Synthesismentioning

confidence: 81%

“…Boronic acids have been demonstrated to serve as an excellent reagent for C-C coupling. [18][19][20] Among our previous studies, [21][22][23][24] a palladium(II)-catalyzed C-C bond formation from arylboronic acid and cyano moiety was investigated. Thus, we assumed that a cross-coupling between boronic acids and α-aroyl aminoacetonitriles would possibly enable a practical approach to unsymmetrical 2,6-disubstituted pyrazines.…”

Section: Synthesismentioning

confidence: 99%

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Palladium(II)-Catalyzed Intramolecular Tandem Cyclization Reaction for the Assembly of Unsymmetrical 2,6-Disubstituted Pyrazines

Chen¹,

Zhu²,

Wang³

et al. 2023

Synthesis

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Section: Synthesismentioning

confidence: 64%

Section: Paper Synthesismentioning

confidence: 81%

Section: Synthesismentioning

confidence: 99%

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Palladium(II)-Catalyzed Intramolecular Tandem Cyclization Reaction for the Assembly of Unsymmetrical 2,6-Disubstituted Pyrazines

Chen¹,

Zhu²,

Wang³

et al. 2023

Synthesis

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“…Palladium metal has been widely employed for the synthesis of various organic compounds 69 as well as for benzofuran dervatives. 70 Luo et al 71 carried out the synthesis of benzoyl-substituted benzofuran heterocycles 22 by treating aryl boronic acid 20 with 2-(2-formylphenoxy) acetonitriles 21 via palladium acetate-catalyzed reaction. A wide range of substituted reactants were employed in standard reaction conditions [(Pd(OAc) 2 (30 mol %) as catalyst, bpy as ligand (30 mol %), toluene as solvent, and at 90 °C] to analyze the substrate scope of this novel synthetic methodology.…”

Section: Precedented Approachesmentioning

confidence: 99%

A Comprehensive Review on Benzofuran Synthesis Featuring Innovative and Catalytic Strategies

Mushtaq,

Zahoor,

Ahmad

et al. 2024

ACS Omega

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Benzofurans have intrigued both pharmaceutical researchers and chemists owing to the medicinal usage of their derivatives against copious diseasecausing agents (i.e., bacteria, viruses, and tumors). These heterocyclic scaffolds are pervasively encountered in a number of natural products and drugs. The everincreasing utilization of benzofuran derivatives as pharmaceutical agents persuaded the chemists to devise novel and facile methodological approaches to assemble the biologically potent benzofuran nucleus. This review summarizes the current developments regarding the innovative synthetic routes and catalytic strategies to procure the synthesis of benzofuran heterocycles with their corresponding mechanistic details, reported by several research groups during 2021−2023.

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“…The first involves a condensation between salicylaldehyde and phenacyl bromide in the presence of a base (Rap–Stoermer reaction). , The second generates arynes in situ in DMF to form o -quinone methides, which then react with α-substituted carbonyls . The third strategy uses a palladium-catalyzed addition of aryl boronic acids to 2-(2-formylphenoxy)ethanenitrile, subsequently undergoing intramolecular aldol condensation to yield benzo[ b ]furans …”

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confidence: 99%

Nickel-Catalyzed Domino Reaction of α-Aryloxyacetonitriles with Arylboronic Acids: Synthesis of 2-Aroylbenzo[b]furans

Subramaniam,

Dharmalingam,

Bhattacharya

et al. 2023

Org. Lett.

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We disclose the first catalytic domino reaction of α-(2-formylaryloxy)acetonitriles with arylboronic acids, yielding a range of 2-aroylbenzo[b]furans with yields of up to 93%. Ni(acac)2 serves as an effective dual catalyst. The protocol is also applicable to α-(2-acetylphenoxy)acetonitrile, giving rise to 3-methyl-2-aroylbenzo[b]furans. This domino process is efficient, additive-free, and compatible with a variety of aryl boronic acids, including those with CF3, NO2, CN, and CO2Me groups. Mechanistic studies highlight the dual activation facilitated by the nickel catalyst.

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Synthesis of 2-Benzoylbenzofurans via Palladium(II)-catalyzed Cascade Reactions

Cited by 3 publications

References 20 publications

Palladium(II)-Catalyzed Intramolecular Tandem Cyclization Reaction for the Assembly of Unsymmetrical 2,6-Disubstituted Pyrazines

Palladium(II)-Catalyzed Intramolecular Tandem Cyclization Reaction for the Assembly of Unsymmetrical 2,6-Disubstituted Pyrazines

A Comprehensive Review on Benzofuran Synthesis Featuring Innovative and Catalytic Strategies

Nickel-Catalyzed Domino Reaction of α-Aryloxyacetonitriles with Arylboronic Acids: Synthesis of 2-Aroylbenzo[b]furans

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