HFIP-Assisted Denitrogenative Radical Fragmentation Pathway of Areneazo-2-(2-nitro)propanes: Cross-Coupling of Aryl Radicals with Alkynes and Coupling Reagents

IF 5 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-07-25 DOI:10.1021/acs.orglett.5c02494

Daeun Kim, Hun Young Kim* and Kyungsoo Oh*,

引用次数: 0

Abstract

The HFIP-assisted denitrogenative radical fragmentation of areneazo-2-(2-nitro)propanes, a safer alternative to diazonium salts, generated dinitrogen, nitrogen monoxide, acetone, and aryl radicals. These in situ generated aryl radicals participated in [4 + 2] benzannulations to form phenanthrenes and in diverse cross-coupling reactions, including Sandmeyer-type C–Br/C–Bpin/C–S/C–Se/C–P and C–C bond formations. TEMPO-trapping experiments confirmed their transient nature, enabling versatile approaches to radical-mediated C–C and C–X bond construction under mild and practical conditions.

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hfip辅助芳烃偶氮-2-（2-硝基）丙烷的脱氮自由基裂解途径：芳基自由基与炔和偶联试剂的交叉偶联。

hfip辅助的芳氮偶氮-2-（2-硝基）丙烷（一种比重氮盐更安全的替代品）的脱氮自由基裂解产生了二氮、一氧化氮、丙酮和芳基自由基。这些原位生成的芳基自由基参与了[4 + 2]苯环形成菲，并参与了多种交叉偶联反应，包括sandmeyer型C-Br/C-Bpin/C-S/C-Se/C-P和C-C键的形成。tempo捕获实验证实了它们的瞬态性质，使自由基介导的C-C和C-X键构建在温和和实用的条件下成为可能。

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.