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Chinese Journal of Organic Chemistry >

2022 , Vol. 42 >Issue 7: 2192 - 2200

DOI: https://doi.org/10.6023/cjoc202203017

ARTICLES

Ru(II)-Catalyzed Regioselective C—H Alkenylation of Indoles Using Cyanomethyl Directing Group

  • Fachao Yan ,
  • Yang Li ,
  • Yudong Li ,
  • Mohamed Makha ,
  • Yuehui Li
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  • aState Key Laboratory for Oxo Synthesis and Selective Oxidation, Suzhou Research Institute of LICP, Lanzhou Institute of Chemical Physics (LICP), Chinese Academy of Sciences, Lanzhou 730000
    bUniversity of Chinese Academy of Sciences, Beijing 100049
† These authors contributed equally to this work
* E-mail:

Received date: 2022-03-06

  Revised date: 2022-03-22

  Online published: 2022-03-30

Supported by

the National Natural Science Foundation of China(22022204); the National Natural Science Foundation of China(21633013); the National Natural Science Foundation of China(22072167)

Fold

Abstract

A ruthenium-catalyzed C(2)-alkenylation of indole derivatives by employing cyanomethyl as the directing group was developed for the first time. Site-selective alkenylation was achieved for a broad scope of alkenes as coupling partners with a large number of indoles bearing synthetically useful functional groups. The protocol represents a novel method for C(2)-alkenylation of indoles affording biologically relevant indolic compounds. The reaction conditions were mild and it showed good substrate scope and functional group compatibility. Ester group, cyano group, iodine, bromine, fluorine and trifluoromethyl were all well compatible. The directing group can be easily removed under relatively mild conditions to form N—H indoles.

Key words： Ru(II)-catalysis; C(2)-alkenylation; indole; cyanomethyl directing group; C—H bond functionalization

Cite this article

Fachao Yan , Yang Li , Yudong Li , Mohamed Makha , Yuehui Li . Ru(II)-Catalyzed Regioselective C—H Alkenylation of Indoles Using Cyanomethyl Directing Group[J]. Chinese Journal of Organic Chemistry, 2022 , 42(7) : 2192 -2200 . DOI: 10.6023/cjoc202203017

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