Synlett
DOI: 10.1055/a-2701-6195
Letter
Published as part of the Special Issue dedicated to Prof. S. Chandrasekaran on his 80th birthday

Cobalt-Catalyzed C-2 Functionalization of N-Methylindole-1-carboxamide via Regioselective Hydroindolation of 1,6-Diyne

Autoren

  • Saista Afreen

    1   School of Chemical Sciences, National Institute of Science Education and Research (NISER), Padanpur, India
    2   Department of Chemistry, Indian Institute of Science Education and Research (IISER), Tirupati, India
  • Abhipsa Ghosh

    1   School of Chemical Sciences, National Institute of Science Education and Research (NISER), Padanpur, India
    2   Department of Chemistry, Indian Institute of Science Education and Research (IISER), Tirupati, India
  • Shyam Kumar Banjare

    1   School of Chemical Sciences, National Institute of Science Education and Research (NISER), Padanpur, India
  • Ponneri C. Ravikumar

    1   School of Chemical Sciences, National Institute of Science Education and Research (NISER), Padanpur, India
    2   Department of Chemistry, Indian Institute of Science Education and Research (IISER), Tirupati, India

We are thankful to NISER, the Department of Atomic Energy (DAE), IISER Tirupati, Science and Engineering Research Board (SERB), New Delhi (Grant CRG/2021/007153) for financial support.


Graphical Abstract

Abstract

In this study, we present the novel reactivity of a cobalt(III) catalyst in the context of the functionalization of 1,6-diynes. Our mechanistic investigation reveals the intrinsic formation of a five-membered cobaltacycle, which subsequently undergoes migratory insertion with 1,6-diynes. Additionally, radical trapping studies provide compelling evidence supporting the involvement of an ionic pathway in this transformation. Furthermore, the deuterium exchange experiment lends further support to our proposed mechanism. Significantly, this methodology exhibits extensive versatility, accommodating a diverse array of electronically distinct substrates and reactive partners in a highly atom-efficient manner.



Publikationsverlauf

Eingereicht: 02. August 2025

Angenommen nach Revision: 14. September 2025

Accepted Manuscript online:
14. September 2025

Artikel online veröffentlicht:
21. Oktober 2025

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