Fluorocyclization of N-Propargyl Carboxamides by λ3-Iodane Catalysts with Coordinating Substituents

Shunsuke Takahashi, Yuki Umakoshi, Kaii Nakayama, Yohei Okada, Viktor V. Zhdankin, Akira Yoshimura, Akio Saito

Research output: Contribution to journalArticlepeer-review

5 Citations (Scopus)

Abstract

Aiming at the enhanced catalytic activity of fluoro-λ3-iodane generated from iodoarene precatalyst with Selectfluor and HF⋅pyridine, this study focused on the λ3-iodanes bearing coordinating substituents. Compared to 4-iodoanisole as a precatalyst of our previous method, N-methyl-2-iodobenzamide or 2-iodobenzamide worked well in the fluorocyclization of N-propargyl carboxamides to oxazoles. Control experiments suggest the equilibrium mixture of iodane-amine complexes and cyclic iodane fluorides would be involved in the present catalysis. (Figure presented.).

Original languageEnglish
Pages (from-to)2997-3003
Number of pages7
JournalAdvanced Synthesis and Catalysis
Volume362
Issue number14
DOIs
Publication statusPublished - 29 Jul 2020
Externally publishedYes

Keywords

  • catalysis
  • cyclization
  • fluorination
  • iodine
  • metal-free

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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