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

Ruhuai Mei, Hui Wang, Svenja Warratz, Stuart A. MacGregor*, Lutz Ackermann

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

116 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. Mit O2: Co(OAc)2 enabled the aerobic C-H/N-H functionalization with O2 as the sole oxidant under Cp∗-free conditions, which enabled step-economical access to anticancer isoquinolones by highly selective C-H activation (see scheme, Cp∗=pentamethylcyclopentadienyl).

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

Keywords

  • annulation
  • C-H activation
  • cobalt
  • density functional calculations
  • isoquinolones
  • oxidase

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