Rhodium(III)-Catalyzed Redox-Neutral [4 + 2] Annulation of 3,5-Diaryloxadiazoles with Alkynes: A Dual C–H Activation Strategy for Constructing C–N Atropisomers

IF 5 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-04-22 DOI:10.1021/acs.orglett.5c0067610.1021/acs.orglett.5c00676

Siyuan Li, Yinsong Han, Zhen Yang, Chen Wang, Ruokun Feng*, Minfeng Zeng*, Zhanxiang Liu and Yuhong Zhang,

引用次数: 0

Abstract

A rhodium(III)-catalyzed dual-ring formation via cascade C–H activation/[4 + 2] annulation of 3,5-diaryoxadiazoles with alkynes was developed. This strategy has been demonstrated with a variety of 3,5-diaryloxadiazoles and alkynes, and it has been successfully scaled up to gram-scale synthesis, highlighting its potential significance in the direct construction of C–N atropisomers. Furthermore, the cleavage of the N–O bond is essential for the formation of the bicyclic structure in the absence of an external oxidant. Mechanistic studies revealed that cleavage of the C–H bond at the 3-phenyl group of oxadiazole was likely a rate-determining step in this reaction.

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铑（III）催化3,5-二乙基氧沙二唑与炔的氧化还原-中性[4 + 2]环化：构建C-N退聚体的双碳氢活化策略

研究了铑（III）催化3,5-二氧恶二唑与炔通过C-H级联活化/[4 + 2]环化形成双环的反应。该策略已在多种3,5-二乙基氧二唑和炔烃中得到证实，并已成功地扩大到克级合成，突出了其在直接构建C-N退聚体方面的潜在意义。此外，在没有外部氧化剂的情况下，N-O键的断裂对于双环结构的形成是必不可少的。机理研究表明，在恶二唑的3-苯基上的C-H键的断裂可能是该反应的速率决定步骤。

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.