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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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