烷基化柱芳烃的CAN氧化直接合成[5]柱醌和[6]柱醌

IF 1.5 4区化学 Q3 CHEMISTRY, ORGANIC

Tetrahedron Letters Pub Date : 2025-07-09 DOI:10.1016/j.tetlet.2025.155739

Venkatesh Bollabathini, Kåre B. Jørgensen

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引用次数: 0

摘要

本文报道了用硝酸铈铵（CAN）在乙腈水溶液中直接氧化烷氧基柱芳烃，简单、高效、高产地合成了柱[n]醌（n = 5和6）。避免卤化溶剂，二甲氧基柱状[5]芳烃在30分钟内转化为柱状[5]醌（产率92%），二氧基柱状[6]芳烃转化为柱状[6]醌（产率90%）。广泛的底物范围允许大多数烷氧基柱状芳烃直接氧化，通过Lewis酸催化直接合成，使柱状醌易于用于未来的反应性和主客体性质探索。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

Direct synthesis of pillar[5]quinone and pillar[6]quinone by CAN oxidation of alkylated pillararenes

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Direct synthesis of pillar[5]quinone and pillar[6]quinone by CAN oxidation of alkylated pillararenes

We report a simple and efficient high-yielding synthesis of pillar[n]quinones (n = 5 and 6) by direct oxidation of alkoxy pillararenes, using ceric ammonium nitrate (CAN) in aqueous acetonitrile. Avoiding halogenated solvents, dimethoxy pillar[5]arene was transformed to pillar[5]quinone (92% yield) and diethoxy pillar[6]arene to pillar[6]quinone (90% yield) in 30 min. A broad substrate scope allows direct oxidation of most alkoxy pillararenes, accessible through a Lewis acid catalyzed direct synthesis, and make pillarquinones readily available for future exploration of reactivity and host-guest properties.

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来源期刊

Tetrahedron Letters 化学-有机化学

CiteScore

3.50

自引率

5.60%

发文量

521

审稿时长

28 days

期刊介绍： Tetrahedron Letters provides maximum dissemination of outstanding developments in organic chemistry. The journal is published weekly and covers developments in techniques, structures, methods and conclusions in experimental and theoretical organic chemistry. Rapid publication of timely and significant research results enables researchers from all over the world to transmit quickly their new contributions to large, international audiences.