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Catalytic Cycloisomerization–Fluorination Sequence of N ‐Propargyl Amides by Iodoarene/HF⋅Pyridine/Selectfluor Systems
Author(s) -
Asari Naoki,
Takemoto Yusuke,
Shinomoto Yukino,
Yagyu Takuma,
Yoshimura Akira,
Zhdankin Viktor V.,
Saito Akio
Publication year - 2016
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201600383
Subject(s) - selectfluor , cycloisomerization , chemistry , catalysis , pyridine , propargyl , iodine , organic chemistry , medicinal chemistry
As a first example of metal‐free and catalytic fluorinative transformations of alkynes, we developed a cycloisomerization–fluorination sequence of N ‐propargyl amides catalyzed by an iodine(III) species. The iodine(III) catalyst is in situ generated from iodoarene as a precatalyst with Selectfluor as a fluorinating oxidant in the presence of HF⋅pyridine.