4.7 Article

Rh(iii)-Catalyzed dienylation and cyclopropylation of indoles at the C4 position with alkylidenecyclopropanes

Journal

ORGANIC CHEMISTRY FRONTIERS
Volume 9, Issue 16, Pages 4287-4293

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/d2qo00763k

Keywords

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Funding

  1. Guangdong Pharmaceutical University [51377005, 51377002]
  2. National Natural Science Foundation of China [22101126]
  3. Medical Scientific Research Foundation of Guangdong Province, China [A2020368]
  4. Science and Technology Program of Guangzhou, China [202102021033]

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This study describes a Rh(iii)-catalyzed C-H functionalization of indoles at the C4 position using alkylidenecyclopropanes (ACPs). By choosing different ACPs as reactants, diene or cyclopropane motifs can be selectively introduced into indoles. The protocol exhibits excellent regioselectivity and broad substrate scope. Scale-up experiments and mechanistic studies were conducted.
Herein, we report a Rh(iii)-catalyzed C-H functionalization of indoles at the C4 position with alkylidenecyclopropanes (ACPs). Motifs of dienes or cyclopropanes could be selectively introduced into indoles by choosing different ACPs. This protocol displayed excellent regioselectivity and broad substrate scope. A scale-up experiment and mechanistic studies were also performed.

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