萘基吡啶- cu （II）催化2-萘胺氧化偶联制备BINAM衍生物。

IF 5 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-08-08 DOI:10.1021/acs.orglett.5c02740

Jonghyeon Lee, Jooyeon Lee, Minwoo Kong, Jiwon Kang, Daeyeon Lee, Jeonghyo Lee*, Min Kim* and Houng Kang*,

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引用次数: 0

摘要

在这项研究中，我们报道了通过铜催化2-氨基萘氧化偶联高效合成1,1'-联萘-2,2'-二胺（BINAM）衍生物。使用具有扩展π体系的配体与Cu（II）和分子氧结合作为末端氧化剂，可以形成各种BINAM衍生物，收率高达84%。机制研究表明，氧化还原途径涉及Cu(II)/Cu(I)循环，并提出了配体和底物之间的π-π相互作用来稳定反应中间体，从而有助于观察到的效率。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

Naphthylpyridyl–Cu(II)-Catalyzed Oxidative Coupling of 2-Naphthylamines to Access BINAM Derivatives

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Naphthylpyridyl–Cu(II)-Catalyzed Oxidative Coupling of 2-Naphthylamines to Access BINAM Derivatives

In this study, we report the efficient synthesis of 1,1′-binaphthyl-2,2′-diamine (BINAM) derivatives via copper-catalyzed oxidative coupling of 2-aminonaphthalenes. The use of a ligand featuring an extended π system in combination with Cu(II) and molecular oxygen as the terminal oxidant enabled the formation of various BINAM derivatives in yields of up to 84%. Mechanistic investigations suggest a redox pathway involving Cu(II)/Cu(I) cycling, and π–π interactions between the ligand and substrate are proposed to stabilize reactive intermediates, thereby contributing to the observed efficiency.

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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.