Nickel-Catalyzed Tandem Dimerization/Hydroheteroarylation of Isoprenes with Heteroarenes

IF 4.7 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2026-10-16 Epub Date: 2026-10-07 DOI:10.1021/acs.orglett.6c03936

Wen-Hui Jin, Rong-Chen Duan, Wei-Can Qiu, Chun-Hui Yan, Hong-Mei Sun

引用次数: 0

Abstract

Herein, we report the first nickel-catalyzed tandem dimerization/hydroheteroarylation of isoprenes with indoles, using a catalytic system consisting of a heteroleptic Ni(II) complex Ni(IPr^*OMe)[P(OEt)₃]Br₂ and a base NaO^tBu. This system provides easy access to a range of C2-substituted cyclic monoterpenoid indoles with high regioselectivity under solvent-free conditions. This tandem transformation shows good compatibility with indoles bearing various functional groups, such as esters, acetals, silanes, and boronate esters. The tandem transformation is also applicable to other heteroarenes, including pyrroles, (benzo)thiophenes, (benzo)furans, benzimidazoles, pyrazoles, quinazolones, imidazo[1,2-a]pyridines, and pyridines.

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镍催化异戊二烯与杂芳烃的串联二聚/水杂芳化反应

摘要本文首次报道了镍催化异戊二烯与吲哚的二聚/氢杂芳化反应，该催化体系由镍（II）配合物Ni(IPr*OMe)[P(OEt)3]Br2和碱NaOtBu组成。在无溶剂条件下，该系统可方便地获得一系列具有高区域选择性的c2取代环单萜吲哚。这种串联转化与含各种官能团的吲哚，如酯、缩醛、硅烷和硼酸酯具有良好的相容性。串联转化也适用于其他杂环芳烃，包括吡咯、（苯并）噻吩、（苯并）呋喃、苯并咪唑、吡唑、喹唑酮、咪唑[1,2-a]吡啶和吡啶。

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.