Cobalt-Catalyzed C(sp2)–C(sp3) Suzuki–Miyaura Cross Coupling

IF 4.9 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2020-09-30 DOI:10.1021/acs.orglett.0c02934

Jacob R. Ludwig, Eric M. Simmons, Steven R. Wisniewski, Paul J. Chirik*

引用次数: 16

Abstract

A cobalt-catalyzed method for the C(sp²)–C(sp³) Suzuki–Miyaura cross coupling of aryl boronic esters and alkyl bromides is described. Cobalt–ligand combinations were assayed with high-throughput experimentation, and cobalt(II) sources with trans-N,N′-dimethylcyclohexane-1,2-diamine (DMCyDA, L¹) produced optimal yield and selectivity. The scope of this transformation encompassed steric and electronic diversity on the aryl boronate nucleophile as well as various levels of branching and synthetically valuable functionality on the electrophile. Radical trap experiments support the formation of electrophile-derived radicals during catalysis.

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钴催化C(sp2) -C (sp3) Suzuki-Miyaura交叉偶联

介绍了一种钴催化芳基硼酯与烷基溴C(sp2) -C (sp3) Suzuki-Miyaura交叉偶联的方法。通过高通量实验对钴配体组合进行了分析，发现反式N,N ' -二甲基环己烷-1,2-二胺(DMCyDA, L1)的钴(II)源产率和选择性最佳。这种转变的范围包括芳基硼酸亲核试剂上的空间和电子多样性，以及亲电试剂上不同层次的分支和合成有价值的功能。自由基陷阱实验支持在催化过程中亲电性自由基的形成。

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.