通过铜催化烯烃的芳基硼化和芳基硅化反应形成3,3'-二取代氧化吲哚。
3,3'-Disubstituted Oxindoles Formation via Copper-Catalyzed Arylboration and Arylsilylation of Alkenes.
作者信息
Liang Ren-Xiao, Chen Ru-Yi, Zhong Chao, Zhu Jia-Wen, Cao Zhong-Yan, Jia Yi-Xia
机构信息
College of Chemical Engineering, State Key Laboratory Breeding Base of Green-Chemical Synthesis Technology, Zhejiang University of Technology, Chaowang Road 18#, Hangzhou 310014, China.
出版信息
Org Lett. 2020 Apr 17;22(8):3215-3218. doi: 10.1021/acs.orglett.0c00999. Epub 2020 Mar 27.
Arylboration and arylsilylation reactions of -(2-iodoaryl)acrylamides with bis(pinacolato)-diboron (Bpin) or PhMeSi-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.
通过使用简单的醋酸铜作为唯一催化剂，开发了 -(2-碘芳基)丙烯酰胺与双(频哪醇硼酸酯)-二硼(Bpin)或苯甲基硅基-Bpin的芳基硼化和芳基硅化反应。以中等至优异的产率获得了一系列含硼或硅烷的3,3'-二取代氧化吲哚。该反应被认为是通过一个多米诺序列进行的，该序列涉及分子间烯烃硼铜化或硅铜化，随后是烷基-Cu中间体与芳基碘的分子内偶联。
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