Palladium-catalyzed decarboxylative [2 + 3] cyclocarbonylation reactions of [60]fullerene: selective synthesis of [60]fullerene-fused 3-vinylcyclopentan-4-ones and cyclopentane-4-carbaldehydes

Liu, Tongxin; Zhang, Chuanjie; Zhang, Pengling; Wang, Xin; Ma, Jinliang; Zhang, Guisheng

doi:10.1039/d2qo01116f

Cited by 7 publications

(1 citation statement)

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“…As one of the important zwitterionic allylpalladium precursors, vinyl methylene cyclic carbonates (VMCCs) were first developed by Zhi et al and employed in [3 + 2] cycloadditions. Subsequently, the research groups of Guo, Yuan, and Zhang further explored the reactivity of these VMCCs, respectively. At present, VMCCs have been utilized in [3+n] cycloadditions, [5+n] cycloadditions, allylic substitutions, and others (Scheme , a).…”

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confidence: 99%

Tandem Allylic Amination/oxa-Michael Addition of Vinyl Methylene Cyclic Carbonates via Palladium-Organo Relay Catalysis

Yang

Huang

et al. 2023

Org. Lett.

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A tandem allylic amination/oxa-Michael addition of vinyl methylene cyclic carbonates (VMCCs) has been developed to construct heterocycles by single palladium catalysis or palladium-organo relay catalysis. In this process, the bisnucleophiles first underwent regioselective allylic amination, and then the second nucleophilic group further completed the hetero-Michael addition reaction to form a series of heterocycles. Among them, the chiral 3,4-dihydro-2H-benzo [b][1,4]oxazines could be produced in medium to high yield with good enantioselectivity under a palladium-organo relay catalysis.

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Tandem Allylic Amination/oxa-Michael Addition of Vinyl Methylene Cyclic Carbonates via Palladium-Organo Relay Catalysis

Yang

Huang

et al. 2023

Org. Lett.

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Synthesis of [60]Fullerene‐Fused Allylbenzofurans via Palladium‐Catalyzed Migration Reaction^†

Liu

Yang

et al. 2023

Chin. J. Chem.

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Comprehensive Summary Chemical functionalization of fullerenes has been an important topic in fullerene chemistry. Herein, an unprecedented Pd‐catalyzed migration reaction of [60]fullerene with allyloxy‐tethered aryl iodides is present for the preparation of novel [60]fullerene‐fused allylbenzofurans. The use of 1,2‐bis(diphenylphosphino)benzene (DPPBz) as a ligand is crucial for the success of the transformation. The reaction shows high chemo‐ and regioselectivity, and is flexible with regard to allyl‐migration site, providing a new and efficient approach to rare [60]fullerene‐fused benzofurans. Control experiments disclose that the reaction most probably undergoes a sequential C—O bond cleavage/allyl‐migration/intermolecular cycloaddition cascade process.

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Functionalization of fullerenes by transition metal catalyzed cyclization reactions: Insights into the mechanisms

Artigas,

Castanyer,

Roglans

et al. 2024

Advances in Organometallic Chemistry

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Palladium-catalyzed decarboxylative [2 + 3] cyclocarbonylation reactions of [60]fullerene: selective synthesis of [60]fullerene-fused 3-vinylcyclopentan-4-ones and cyclopentane-4-carbaldehydes

Abstract: Herein, a new palladium-catalyzed decarboxylative [2 + 3] cycloaddition strategy has been developed toward direct cyclocarbonylation of [60]fullerene. Take advantage of this protocol, a series of novel [60]fullerene-fused 3-vinylcyclopentan-4-ones and...

Cited by 7 publications

References 76 publications

Tandem Allylic Amination/oxa-Michael Addition of Vinyl Methylene Cyclic Carbonates via Palladium-Organo Relay Catalysis

Tandem Allylic Amination/oxa-Michael Addition of Vinyl Methylene Cyclic Carbonates via Palladium-Organo Relay Catalysis

Synthesis of [60]Fullerene‐Fused Allylbenzofurans via Palladium‐Catalyzed Migration Reaction^†

Functionalization of fullerenes by transition metal catalyzed cyclization reactions: Insights into the mechanisms

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Palladium-catalyzed decarboxylative [2 + 3] cyclocarbonylation reactions of [60]fullerene: selective synthesis of [60]fullerene-fused 3-vinylcyclopentan-4-ones and cyclopentane-4-carbaldehydes

Abstract: Herein, a new palladium-catalyzed decarboxylative [2 + 3] cycloaddition strategy has been developed toward direct cyclocarbonylation of [60]fullerene. Take advantage of this protocol, a series of novel [60]fullerene-fused 3-vinylcyclopentan-4-ones and...

Cited by 7 publications

References 76 publications

Tandem Allylic Amination/oxa-Michael Addition of Vinyl Methylene Cyclic Carbonates via Palladium-Organo Relay Catalysis

Tandem Allylic Amination/oxa-Michael Addition of Vinyl Methylene Cyclic Carbonates via Palladium-Organo Relay Catalysis

Synthesis of [60]Fullerene‐Fused Allylbenzofurans via Palladium‐Catalyzed Migration Reaction†

Functionalization of fullerenes by transition metal catalyzed cyclization reactions: Insights into the mechanisms

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Synthesis of [60]Fullerene‐Fused Allylbenzofurans via Palladium‐Catalyzed Migration Reaction^†