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Fluorocyclization of N ‐Propargyl Carboxamides by λ 3 ‐Iodane Catalysts with Coordinating Substituents
Author(s) -
Takahashi Shunsuke,
Umakoshi Yuki,
Nakayama Kaii,
Okada Yohei,
Zhdankin Viktor V.,
Yoshimura Akira,
Saito Akio
Publication year - 2020
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.202000381
Subject(s) - chemistry , catalysis , selectfluor , propargyl , pyridine , amine gas treating , medicinal chemistry , combinatorial chemistry , organic chemistry
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.