3,3′-Disubstituted Oxindoles Formation via Copper-Catalyzed Arylboration and Arylsilylation of Alkenes,Organic Letters

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3,3′-Disubstituted Oxindoles Formation via Copper-Catalyzed Arylboration and Arylsilylation of Alkenes
Organic Letters ( IF 4.9 ) Pub Date : 2020-03-27 , DOI: 10.1021/acs.orglett.0c00999
Ren-Xiao Liang ₁ , Ru-Yi Chen ₁ , Chao Zhong ₁ , Jia-Wen Zhu ₁ , Zhong-Yan Cao ₁ , Yi-Xia Jia ₁

Affiliation

Arylboration and arylsilylation reactions of N-(2-iodoaryl)acrylamides with bis(pinacolato)-diboron (B₂pin₂) or PhMe₂Si-Bpin are developed by using simple CuOAc as the sole catalyst. A range of boron- or silane-bearing 3,3′-disubstituted oxindoles are obtained in moderate to excellent yields. The reaction is proposed to proceed via a domino sequence involving intermolecular olefin borylcupration or silylcupration followed by intramolecular coupling of an alkyl-Cu intermediate with aryl iodide.

中文翻译：

铜催化的芳基硼化和芳基甲硅烷基化反应形成3,3'-二取代的吲哚

以简单的CuOAc为唯一催化剂，开发了N-（2-碘芳基）丙烯酰胺与双（频哪醇）-二硼（B ₂ pin ₂）或PhMe ₂ Si-Bpin的芳基硼化和芳基甲硅烷基化反应。以中等至优异的产率获得了一系列含硼或硅烷的3,3'-二取代的羟吲哚。提出该反应通过多米诺序列进行，该多米诺序列包括分子间烯烃的硼基升高或甲硅烷基升高，然后将烷基-Cu中间体与芳基碘化物分子内偶联。

更新日期：2020-04-24

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