Cobalt-Catalyzed Regioselective Direct C-4 Alkenylation of 3-Acetylindole with Michael Acceptors Using a Weakly Coordinating Functional Group
Cobalt-Catalyzed Regioselective Direct C-4 Alkenylation of 3-Acetylindole with Michael Acceptors Using a Weakly Coordinating Functional Group
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DOI：
10.1021/acs.orglett.9b03243
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发表时间：
2019-10-04
期刊：
影响因子：
5.2
通讯作者：
Ravikumar, P. C.
中科院分区：
文献类型：
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作者：
Banjare, Shyam Kumar;Nanda, Tanmayee;Ravikumar, P. C.
在此，我们公开了关于使用第一行过渡金属钴的3-乙酰基吲哚衍生物的选择性C（4）-H官能化的第一个报告，其中乙酰基充当弱配位导向基团。通过简单地将添加剂从乙酸铜转换为碳酸银，使用不同的迈克尔受体（丙烯酸酯和马来酰亚胺）实现了选择性C（4）-H官能化。此外，还通过HRMS检测到acobaltaclide中间体的形成，以了解机理。
Herein, we disclosed the first report on the selective C(4)-H functionalization of 3-acetylindole derivatives using first-row transition metal cobalt where an acetyl group is acting as a weakly coordinating directing group. Selective C(4)-H functionalization has been achieved using diverse Michael acceptors (acrylate and maleimide) simply by switching the additive from copper acetate to silver carbonate. Further the formation of acobaltacycle intermediate was also detected through HRMS for mechanistic insight.