Cobalt-Catalyzed Oxidase C-H/N-H Alkyne Annulation: Mechanistic Insights and Access to Anticancer Agents

Ruhuai Mei, Hui Wang, Svenja Warratz, Stuart Alan Macgregor, Lutz Ackermann

Research output: Contribution to journalArticle

81 Citations (Scopus)

Abstract

Cp*-free cobalt-catalyzed alkyne annulations by C-H/N-H functionalizations were accomplished with molecular O2 as the sole oxidant. The user-friendly oxidase strategy proved viable with various internal and terminal alkynes through kinetically relevant C-H cobaltation, providing among others step-economical access to the anticancer topoisomerase-I inhibitor 21,22-dimethoxyrosettacin. DFT calculations suggest that electronic effects control the regioselectivity of the alkyne insertion step.

Original languageEnglish
Pages (from-to)6759–6763
Number of pages5
JournalChemistry - A European Journal
Volume22
Issue number20
Early online date8 Apr 2016
DOIs
Publication statusPublished - 10 May 2016

Keywords

  • Annulation
  • C-H activation
  • Cobalt
  • Density functional calculations
  • Isoquinolones
  • Oxidase

ASJC Scopus subject areas

  • Chemistry(all)

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