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

2 Scopus citations

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 (US)
Pages (from-to)2997-3003
Number of pages7
JournalAdvanced Synthesis and Catalysis
Volume362
Issue number14
DOIs
StatePublished - Jul 29 2020

Bibliographical note

Funding Information:
This work was supported partly by JSPS Fund for the Promotion of Joint International Research (Grant No 16KK0199) and JST CREST (No. JPMJCR19R2). V.V.Z. and A.Y. are thankful to National Science Foundation (CHE‐1759798).

Publisher Copyright:
© 2020 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

Keywords

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

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