Intermolecular Double C–H Annulation via 1,4-Pd Migration: A Modular Strategy for Heteropolycycle Construction

IF 5 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-09-19 DOI:10.1021/acs.orglett.5c03264

Zhendong Cheng, , , Siqi Li, , , Yanling Zhang, , , Zhiwei Li, , , Yun Liang*, , and , Yuan Yang*,

引用次数: 0

Abstract

Herein, we report a 1,4-Pd migration-enabled intermolecular double C–H annulation between alkene-tethered aryl halides (e.g., 2-iodo-N-methacryloylbenzamides and 2-(2-iodophenyl)-1H-indoles) and 1,n-diynes. This transformation proceeds through a cascade sequence involving Heck cyclization, alkyl-to-aryl 1,4-Pd migration, double alkyne insertion, and C–H activation, enabling the remote construction of structurally diverse heteropolycycles, including tetracyclic fused isoquinolinediones and hexacyclic indolo[2,1-a]isoquinolinones. The method exhibits a broad substrate scope and excellent regioselectivity.

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通过1,4- pd迁移的分子间双碳氢环：杂多环构建的模块化策略。

在这里，我们报道了在烯系芳基卤化物（例如，2-碘- n-甲基丙烯基苯酰胺和2-（2-碘苯基）- 1h -吲哚）和1，n-二炔之间的1,4- pd迁移激活的分子间双碳氢环。这种转化通过一个级联序列进行，包括Heck环化、烷基到芳基1,4- pd迁移、双炔插入和C-H活化，从而能够远程构建结构多样的杂多环，包括四环融合异喹啉二酮和六环吲哚[2,1-a]异喹啉酮。该方法具有广泛的底物范围和良好的区域选择性。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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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.