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

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...

Full description

Saved in:
Bibliographic Details
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 Heidelberg Wiley Subscription Services, Inc 29.07.2020
Subjects
Catalysis
Catalytic activity
cyclization
Fluorides
fluorination
iodine
metal-free
Online AccessGet full text

Cover

More Information
Summary: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.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.202000381