Nickel-Catalyzed Regioselective Ring-Opening Hydroarylation of Methylenecyclopropanes.

IF 5 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-05-13 DOI:10.1021/acs.orglett.5c01238

Aishuang Fan,Xinyi Li,Jinyang Chen,Yuan-Qing Xu,Shengnan Jin,Zhong-Yan Cao

引用次数: 0

Abstract

The hydroarylation of methylenecyclopropanes (MCPs) is a challenging process due to the difficulty in controlling regioselectivity and the complex reaction patterns involved. Herein, we report a simple external ligand-free Ni-catalyzed ring-opening hydroarylation of MCPs with high efficiency and unprecedented regioselective arylation as well as broad functional group tolerance by using inexpensive aryl boronic acids as the arylation source. The synthetic utility has been demonstrated for the facile preparation of versatile highly valued products. Mechanistic studies suggest that Ni(II)-H, formed via the oxidative addition of Ni(0) to the proton in the system, might act as a key intermediate.

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镍催化甲基环丙烷的区域选择性开环氢芳基化反应。

甲基环丙烷（MCPs）的氢化芳基化是一个具有挑战性的过程，因为难以控制区域选择性和所涉及的复杂反应模式。本文报道了一种简单的无外部配体镍催化的MCPs开环羟基化反应，该反应效率高，具有前所未有的区域选择性和广泛的官能团耐受性，使用廉价的芳基硼酸作为芳基化源。该合成用途已被证明可以方便地制备多功能高价值产品。机理研究表明，Ni(II)-H是由Ni(0)在体系中的质子上氧化加成而形成的，可能是一个关键的中间体。

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.