铜(I)催化骨架重排驱动1,11-二炔环异构化。

IF 5 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-07-26 DOI:10.1021/acs.orglett.5c02326

Jin-Qi Zhang, Qing-Mei Li, Shi-Lang Chen, Hui-Jing Li, Chun-Hua Chen*, Xin-Xian Zhong* and Dong-Liang Mo*,

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引用次数: 0

摘要

在此，我们报道了铜(I)催化的骨架重排驱动的1,11-二炔的环异构化反应。该方法采用含1,11-二炔的o -丙炔肟，以高收率和高区域选择性提供了高效的功能化色基[4,3-b]吡咯。机理研究表明，1,11-达因的环异构化在一锅反应中经历了铜催化的[2,3]重排、顺序的[3 + 2]环加成和[3,3]重排。各种衍生的环异构化产物也已被证明。本方法具有底物范围广、官能团耐受性好、形成2环和5个C-C/C-N/C-O键的特点，是1,11-二炔环异构化的第一个实例。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

Copper(I)-Catalyzed Skeletal Rearrangement-Driven Cycloisomerization of 1,11-Diynes

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Copper(I)-Catalyzed Skeletal Rearrangement-Driven Cycloisomerization of 1,11-Diynes

Herein, we report a copper(I)-catalyzed skeletal rearrangement-driven cycloisomerization of 1,11-diynes under a mild reaction. This method adopts O-propargyl oxime-containing 1,11-diynes and provides efficient access to functionalized chromeno[4,3-b]pyrroles in high yields and high regioselectivity. Mechanistic studies revealed that the cycloisomerization of 1,11-dynes underwent copper-catalyzed [2,3] rearrangement, sequential [3 + 2] cycloaddition, and [3,3] rearrangement in a one-pot reaction. Diverse derivations of the cycloisomerization products have also been demonstrated. The present method features a broad substrate scope and good functional group tolerance, two ring and five C–C/C–N/C–O bond formation, and the first example of cycloisomerization of 1,11-diynes.

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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.