Group-Directed [5+2] Cycloaddition Approach to 10π-Electron Cyclohepta[<i>c</i>]furans and Derivatives

We present a group-assisted protocol that enables the 1,3-dien-5-yne scaffold as a novel five-carbon synthon to accomplish a palladium-catalyzed [5+2] cycloaddition with a variety of alkynes in the presence of H<sub>2</sub>O. This method affords a straightforward approach to the synthesis of 10π-electron 6<i>H</i>-cyclohepta[<i>c</i>]furans that are versatile building blocks for constructing diverse cycloheptatriene-fused molecular architectures.

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Publication Details

Journal
Organic Letters
Published
2025-05-14
DOI
https://doi.org/10.1021/acs.orglett.5c01515
Primary Topic
Catalytic Alkyne Reactions
Type
article
Field-Weighted Citation Impact
0.00

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article

Group-Directed [5+2] Cycloaddition Approach to 10π-Electron Cyclohepta[c]furans and Derivatives

Tianyong Hou, Wenpeng Lü, Yi Yang, Zhen Zhang et al.
Organic Letters
Catalytic Alkyne Reactions
article

Group-Directed [5+2] Cycloaddition Approach to 10π-Electron Cyclohepta[c]furans and Derivatives

Tianyong Hou, Wenpeng Lü, Yi Yang, Zhen Zhang, Cheng Ma
article en

Abstract

We present a group-assisted protocol that enables the 1,3-dien-5-yne scaffold as a novel five-carbon synthon to accomplish a palladium-catalyzed [5+2] cycloaddition with a variety of alkynes in the presence of H<sub>2</sub>O. This method affords a straightforward approach to the synthesis of 10π-electron 6<i>H</i>-cyclohepta[<i>c</i>]furans that are versatile building blocks for constructing diverse cycloheptatriene-fused molecular architectures.

Organic LettersVol. 27(20)
Zhejiang University (CN)
National Natural Science Foundation of China
Openalex Percentile: Top 92%
Catalytic Alkyne Reactions
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Group-Directed [5+2] Cycloaddition Approach to 10π-Electron Cyclohepta[<i>c</i>]furans and Derivatives — Tianyong Hou, Wenpeng Lü, et al. · Organic Letters (2025) | TGRS Research Map | TGRS