From Benzofurans to Indoles: Palladium‐Catalyzed Reductive Ring‐Opening and Closure <i>via</i> β‐Phenoxide Elimination

Perego, Luca Alessandro; Wagschal, Simon; Grüber, R.; Fleurat‐Lessard, Paul; Kaı̈m, Laurent El; Grimaud, Laurence

doi:10.1002/adsc.201801225

Cited by 9 publications

(3 citation statements)

References 88 publications

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“…The authors have cited additional references within the Supporting Information. [25][26][27][28][29][30][31][32][33][34][35][36][37][38][39]…”

Section: Supporting Informationmentioning

confidence: 99%

Iron‐Catalyzed C−H Alkylation/Ring Opening with Vinylbenzofurans Enabled by Triazoles

Cattani,

Pandit,

Buccio

et al. 2024

Angewandte Chemie

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We report an unprecedented iron‐catalyzed C−H annulation using readily available 2‐vinylbenzofurans as the reaction pattern. The redox‐neutral strategy, based on cheap, non‐toxic and earth abundant iron catalysts, exploits triazole assistance to promote a cascade C−H alkylation, benzofuran ring‐opening and insertion into a Fe−N bond, to form highly functionalized isoquinolones. Detailed mechanistic studies supported by DFT calculations fully disclosed the manifold of the iron catalysis.

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“…The authors have cited additional references within the Supporting Information. [25][26][27][28][29][30][31][32][33][34][35][36][37][38][39]…”

Section: Supporting Informationmentioning

confidence: 99%

Iron‐Catalyzed C−H Alkylation/Ring Opening with Vinylbenzofurans Enabled by Triazoles

Cattani,

Pandit,

Buccio

et al. 2024

Angewandte Chemie

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“…In 2019, Grimaud and colleagues utilized microwave‐assisted synthesis achieved the ring‐opening of benzofurans by a palladium‐catalyzed process at 130 °C in propionitrile solvent, to afford the indole derivatives in good yields (Scheme 22). [36] Those transformations are initated by the oxidative addition of aryl iodide into Pd(0) to generate Int. 21‐A , after the double bond of benzofuran migration insertion of phenylpalladium species, a crucial intermediate 21‐B is obtained.…”

Section: Metal Catalyzed Ring‐opening Of Benzofuranmentioning

confidence: 99%

The Ring‐Opening Reaction of Benzofuran Involving the Cleavage of C−O Bond

Yu,

Huang

2023

ChemCatChem

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Ring‐opening of (di)benzofurans is a significant area of research in organic chemistry, offering versatile and direct synthetic strategies to access valuable functional phenol derivatives. Transition metal catalysis, particularly nickel‐catalyzed reactions, has been extensively explored for the selective cleavage of the C–O bond in (di)benzofuran. Metal‐free methods, such as acid catalysis and strong base‐mediated process, have also emerged as important alternatives. Organometallic reagents, including Grignard and organolithium reagents, play a pivotal role in promoting efficient C–O bond activation. The field of (di)benzofuran ring opening holds great promise for the synthesis of complex molecules with diverse applications in pharmaceuticals, materials science, and fine chemical synthesis. Continued research efforts will pave the way for innovative strategies and broaden the utility of (di)benzofuran derivatives in various fields.

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“…The authors have cited additional references within the Supporting Information. [25][26][27][28][29][30][31][32][33][34][35][36][37][38][39][40][41][42][43][44]…”

Section: Supporting Informationmentioning

confidence: 99%

Photocatalytic Dearomative Intermolecular Seven‐Membered Ring Construction of Benzofurans

Harada,

Yamamoto,

Okabe

et al. 2023

Asian J Org Chem

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We report the synthesis of seven‐membered carbocycles through the dearomative intermolecular reaction of benzofurans with vinylcyclopropanes. The significant feature of this method involves activating benzofurans through energy transfer from an activated photocatalyst. Substituent effects were investigated for each substrate, and hydrocyclohepta[b]benzofurans with a tetrasubstituted carbon were obtained as a single diastereomer. This synthetic approach compliments the reported methodologies for synthesizing this type of skeleton and introduces a new feedstock for this skeleton with a different substitution pattern. Computational studies of the reaction mechanism suggested that the reaction proceeds stepwise through addition, small ring opening, and re‐cyclization. This novel synthetic approach opens up new possibilities for efficiently constructing seven‐membered carbocycles. Moreover, it provides a valuable platform for discovering unique molecules with diverse substitution patterns.

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From Benzofurans to Indoles: Palladium‐Catalyzed Reductive Ring‐Opening and Closure via β‐Phenoxide Elimination

Cited by 9 publications

References 88 publications

Iron‐Catalyzed C−H Alkylation/Ring Opening with Vinylbenzofurans Enabled by Triazoles

Iron‐Catalyzed C−H Alkylation/Ring Opening with Vinylbenzofurans Enabled by Triazoles

The Ring‐Opening Reaction of Benzofuran Involving the Cleavage of C−O Bond

Photocatalytic Dearomative Intermolecular Seven‐Membered Ring Construction of Benzofurans

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