Gold-Catalyzed Intermolecular Assembly of Donor and Acceptor Fragments for [1,5]-Hydride Migrations

IF 5 1区化学 Q1 CHEMISTRY, ORGANIC Organic Letters Pub Date : 2025-03-20 DOI:10.1021/acs.orglett.5c00816

Xiao-Qian Zhang, Ningbo Li, Yongliang Zhang, Youliang Wang

引用次数: 0

Abstract

The [1,n]-hydride migration reactions represent one of the most powerful techniques to functionalize C(sp³)–H bonds and to rapidly construct molecular complexities. However, their substrates usually required multiple steps to prepare in advance. Herein, we developed a gold-catalyzed intermolecular coupling of hydride-donor-containing nucleophiles (amines) and hydride-acceptor-containing alkynes (1,3-diynamides) for cascade [1,5]-hydride migrations. Control experiments revealed the role of the dichloroethane solvent and the unexpected involvement of protonated anilines in promoting [1,5]-hydride migrations.

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金催化的[1,5]-氢化物迁移供体和受体片段的分子间组装

[1,n]-酸酐迁移反应是官能化 C（sp3）-H 键和快速构建复杂分子的最强大技术之一。然而，其底物通常需要多个步骤才能提前制备。在此，我们开发了一种金催化的含氢化物供体的亲核物（胺）和含氢化物受体的炔类（1,3-二炔酰胺）分子间偶联反应，用于级联 [1,5]- 氢迁移。对照实验揭示了二氯乙烷溶剂的作用以及质子化苯胺在促进 [1,5]- 酸酐迁移中的意外参与。

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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.