Fluorocyclization of N ‐Propargyl Carboxamides by λ 3 ‐Iodane Catalysts with Coordinating Substituents

Abstract Aiming at the enhanced catalytic activity of fluoro‐λ 3 ‐iodane generated from iodoarene precatalyst with Selectfluor and HF⋅pyridine, this study focused on the λ 3 ‐iodanes bearing coordinating substituents. Compared to 4‐iodoanisole as a precatalyst of our previous method, N ‐methyl‐2‐iod...

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Published inAdvanced synthesis & catalysis Vol. 362; no. 14; pp. 2997 - 3003
Main Authors Takahashi, Shunsuke, Umakoshi, Yuki, Nakayama, Kaii, Okada, Yohei, Zhdankin, Viktor V., Yoshimura, Akira, Saito, Akio
Format Journal Article
LanguageEnglish
Published 29.07.2020
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Summary:Abstract Aiming at the enhanced catalytic activity of fluoro‐λ 3 ‐iodane generated from iodoarene precatalyst with Selectfluor and HF⋅pyridine, this study focused on the λ 3 ‐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. magnified image
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.202000381