Electrooxidative Ring-Opening Transformation of Polycyclic Aromatic Hydrocarbons.

IF 5 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-10-20 DOI:10.1021/acs.orglett.5c03446

Ryosuke Sakamoto,Kei Muto,Junichiro Yamaguchi

引用次数: 0

Abstract

Cleavage of aromatic C-C bonds remains a formidable challenge in organic synthesis due to their exceptional stability. We describe an electrooxidative protocol that enables selective cleavage of peripheral C-C bonds in various polycyclic aromatic hydrocarbons (PAHs) under anodic oxidation conditions in DMF, affording dicarbonyl products. In addition to phenacenes, this method cleaves the peripheral bond of corannulene and the inner bond of dibenzo[g,p]chrysene, demonstrating a broad applicability for PAH bond activation.

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多环芳烃的电氧化开环转化。

芳香族C-C键由于其特殊的稳定性，在有机合成中切割仍然是一个艰巨的挑战。我们描述了一种电氧化协议，可以在DMF的阳极氧化条件下选择性地切割各种多环芳烃（PAHs）的外周C-C键，从而产生二羰基产物。除苯类外，该方法还切割了环烯的外键和二苯并[g，p]芘的内键，证明了对多环芳烃键激活的广泛适用性。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Organic Letters 化学-有机化学

CiteScore

9.30

自引率

11.50%

发文量

1607

审稿时长

1.5 months

期刊介绍： Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.