Photoredox Catalyzed Conia-Ene-Type Cyclization/Smiles Rearrangement Cascade Reactions to Access Substituted Methylenecarbocycles,Organic Letters

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Photoredox Catalyzed Conia-Ene-Type Cyclization/Smiles Rearrangement Cascade Reactions to Access Substituted Methylenecarbocycles
Organic Letters ( IF 4.9 ) Pub Date : 2024-09-11 , DOI: 10.1021/acs.orglett.4c03033
Keyuan Zhang ₁ , Qi Jiang ₁ , Chonglong He ₁ , Mingyou Hu ₁ , Yangyang Cheng ₂ , Xin-Hua Duan ₁ , Le Liu ₁

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We report a novel visible-light-driven photoredox-catalyzed cascade reaction involving Conia-ene-type cyclization and Smiles rearrangement initiated from alkyne-tethered α-sulfonyl esters. This methodology not only facilitates the rapid synthesis of a broad spectrum of highly substituted methylenecarbocycles but also introduces a new mechanistic pathway with aryl group migration, surpassing the conventional 1,5-hydrogen shift typically observed in Conia-ene reactions.

中文翻译：

光氧化还原催化 Conia-Ene 型环化/Smile 重排级联反应以获得取代的亚甲基碳环

我们报告了一种新型可见光驱动的光氧化还原催化级联反应，涉及从炔烃束缚的 α-磺酰酯引发的 Conia 烯型环化和 Smiles 重排。该方法不仅促进了广谱高度取代的亚甲基碳环的快速合成，而且引入了一种新的芳基迁移机制途径，超越了 Conia-ene 反应中通常观察到的传统 1,5-氢转移。

更新日期：2024-09-11

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