Rhodium(III)‐Catalyzed Regioselective C‐H Allylation and Prenylation of Indoles at C4‐Position Using a Weak Coordinating Group
Rhodium(III)‐Catalyzed Regioselective C‐H Allylation and Prenylation of Indoles at C4‐Position Using a Weak Coordinating Group
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DOI：
10.1002/adsc.202100882
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发表时间：
2021-10
影响因子：
5.4
通讯作者：
Shang‐Shi Zhang;Yan-Zhi Liu;Yi-Chuan Zheng;Huiyuan Xie;Shaojun Chen;Jia-lin Song;Bing Shu
中科院分区：
文献类型：
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作者：
Shang‐Shi Zhang;Yan-Zhi Liu;Yi-Chuan Zheng;Huiyuan Xie;Shaojun Chen;Jia-lin Song;Bing Shu
在此，Rh（III）催化的吲哚的C4-选择性C-H烯丙基化和异戊二烯化通过使用弱羰基配位导向基团已经被报道。通过使用5-亚甲基-1，3-二氧杂环己-2-酮、4-乙烯基-1，3-二氧杂环戊-2-酮和2-甲基-2，3-丁二烯作为可扩展的交叉偶联配偶体，这些不同的合成方案在氧化还原中性反应条件下顺利进行，以中等至满意的产率提供各种烯丙基化和异戊二烯化吲哚。这种转化表现出高官能团相容性和广泛的底物范围。并进行了放大实验和机理研究。
Herein, Rh(III)‐catalyzed C4‐selective C−H allylation and prenylation of indoles by using a weak carbonyl coordination directing group have been reported. By employing 5‐methylene‐1,3‐dioxan‐2‐ones, 4‐vinyl‐1,3‐dioxolan‐2‐ones and 2‐methyl‐2,3‐butadiene as scalable cross‐coupling partners, these divergent synthesis protocols proceed smoothly under redox‐neutral reaction conditions, delivering various allylated and prenylated indoles in moderate to satisfied yields. This transformation exhibits high functional‐groups compatibility and broad substrate scope. Scale‐up experiment and mechanistic studies were also accomplished.