Transition Metal‐Catalyzed Intermolecular Hydroarylation of Allenes

Pagès, Lucas; Abdine, Racha Abed Ali; Monnier, Florian; Taillefer, Marc

doi:10.1002/ejoc.202200724

Eur J Org Chem

2022

DOI: 10.1002/ejoc.202200724

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Transition Metal‐Catalyzed Intermolecular Hydroarylation of Allenes

Lucas Pagès

Racha Abed Ali Abdine

Florian Monnier

et al.

Abstract: Scheme 1. Transition metal-catalyzed intermolecular hydroarylation of allenes. Scheme 2. Platinum-catalyzed hydroarylation of 1,1-dimethylallene with phenols. Scheme 3. Proposed mechanism for Pt-catalyzed hydroarylation of 1,1dimethylallene with phenols. Scheme 4. Scandium-catalyzed hydroarylation of allenic ketones with indoles. Scheme 5. Scandium-catalyzed hydroarylation of monosubstituted allenes with pyridines. Scheme 6. Possible mechanism for Sc-catalyzed hydroarylation of monosubstituted allenes with pyr… Show more

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Cited by 6 publications

References 74 publications

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Three Component Cascade Processes Involving Palladium Catalyzed Transformations/Dipolar Cycloadditions for the Synthesis of Angular Heterotriquinane Derivatives

Jovanovic,

Petkovic

et al. 2024

Adv Synth Catal

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Combining chemical reactivities of allenes and oximes created a methodology for the preparation of heterocyclic triquinane‐type skeletons via a cascade process constructing four bonds in a single step. The initial reaction of allene moiety promoted by Pd‐catalysis, affording π‐allyl Pd‐species, was followed by two additional transformations ‐ nucleophilic displacement and dipolar cycloaddition ‐ to furnish the product highly stereoselectively in moderate to good yields. For the process to be efficient, it was necessary to use a dipolarophilic component as a solvent. Intriguingly, while the reaction with cyclopentanone derived oxime progressed through the whole cascade, with cyclohexanone analogue it stopped at the nitrone stage, requiring an additional step to yield similar type of products. Some aspects of the studied cascade were examined by DFT.

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Three Component Cascade Processes Involving Palladium Catalyzed Transformations/Dipolar Cycloadditions for the Synthesis of Angular Heterotriquinane Derivatives

Jovanovic,

Petkovic

et al. 2024

Adv Synth Catal

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show abstract

Skeletal and Mechanistic Diversity in Ir‐Catalyzed Cycloisomerizations of Allene‐Tethered Pyrroles and Indoles

Arribas,

Calvelo,

Rey

et al. 2024

Angewandte Chemie

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Pyrroles and indoles bearing N‐allenyl tethers participate in a variety of iridium‐catalyzed cycloisomerization processes initiated by a C‐H activation step, to deliver a diversity of synthetically relevant azaheterocyclic products. By appropriate selection of the ancillary ligand and the substitution pattern of the allene, the reactions can diverge from simple intramolecular hydrocarbonations to tandem processes involving intriguing mechanistic issues. Accordingly, a wide range of heterocyclic structures ranging from dihydro‐indolizines and pyridoindoles to tetrahydroindolizines, as well as cyclopropane‐fused tetrahydroindolizines can be obtained. Moreover, by using chiral ligands, these cascade processes can be carried out in an enantioselective manner. DFT studies provide insights into the underlying mechanisms and justify the observed chemo‐ regio‐ and stereoselectivities.

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Skeletal and Mechanistic Diversity in Ir‐Catalyzed Cycloisomerizations of Allene‐Tethered Pyrroles and Indoles

Arribas,

Calvelo,

Rey

et al. 2024

Angew Chem Int Ed

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Transition Metal‐Catalyzed Intermolecular Hydroarylation of Allenes

Cited by 6 publications

References 74 publications

Three Component Cascade Processes Involving Palladium Catalyzed Transformations/Dipolar Cycloadditions for the Synthesis of Angular Heterotriquinane Derivatives

Three Component Cascade Processes Involving Palladium Catalyzed Transformations/Dipolar Cycloadditions for the Synthesis of Angular Heterotriquinane Derivatives

Skeletal and Mechanistic Diversity in Ir‐Catalyzed Cycloisomerizations of Allene‐Tethered Pyrroles and Indoles

Skeletal and Mechanistic Diversity in Ir‐Catalyzed Cycloisomerizations of Allene‐Tethered Pyrroles and Indoles

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