有机光氧化还原/钴双催化四氢萘的析氢偶氮化/芳构化反应

IF 5 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-03-27 DOI:10.1021/acs.orglett.5c0064010.1021/acs.orglett.5c00640

Cheng Huang*, Sheng Tang, Chen-Lu Wang, Chen Kang, Ying Wang, Yaru Jing, Zhong-Ming Ye, Zhenhong Wei and Hu Cai*,

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引用次数: 0

摘要

本文报道了一种光氧化还原/钴肟双催化方法，用于四氢萘的串联脱氢偶氮化和芳构化，以快速构建N-（β-萘基）唑结构。该方案强调贵金属无和外部氧化剂无条件，步骤和原子经济，和位点选择性。初步的机理研究发现，在可见光照射下，饱和萘代物发生了n中心自由基介导的C-H / N-H交叉偶联，然后脱氢芳构化，DFT计算阐明了位点选择性。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

Tandem Azolation/Aromatization of Tetrahydronaphthalenes with Hydrogen Evolution via Organophotoredox/Cobalt Dual Catalysis

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Tandem Azolation/Aromatization of Tetrahydronaphthalenes with Hydrogen Evolution via Organophotoredox/Cobalt Dual Catalysis

Reported herein is a photoredox/cobaloxime dual-catalytic approach to execute tandem dehydrogenative azolation and aromatization of tetrahydronaphthalene for rapid construction of N-(β-naphthyl)azole architectures. This protocol highlights noble metal-free and external oxidants-free conditions, step- and atom-economy, and site-selectivity. A preliminary mechanistic study has uncovered that the transformation undergoes a N-centered radical mediated C–H/N–H cross-coupling followed by dehydrogenative aromatization of saturated naphthyl surrogates under visible light irradiation, and DFT calculations elucidate the site-selectivity.

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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.