Premium
PhIO/Et 3 N ⋅ 3HF‐Mediated Formation of Fluorinated 2 H ‐Azirines via Domino Fluorination/Azirination Reaction of Enamines
Author(s) -
Zhang Yong,
Zhao Xiaoyuan,
Zhuang Chen,
Wang Senlin,
ZhangNegrerie Daisy,
Du Yunfei
Publication year - 2018
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.201800124
Subject(s) - chemistry , enamine , hypervalent molecule , domino , reagent , fluorine , combinatorial chemistry , medicinal chemistry , organic chemistry , catalysis
A variety of enamine carboxylic esters and enaminones were converted to the biologically interesting fluorinated 2 H ‐azirines through reactions with PhIF 2 generated in situ by PhIO and Et 3 N ⋅ 3HF in 1,2‐dichroloethane, which features the hypervalent iodine reagents‐mediated introduction of fluorine atom and formation of the 2 H ‐azirine skeleton under metal‐free conditions. The domino reaction is postulated to proceed via a PhIF 2 ‐mediated oxidative fluorination and a subsequent azirination of the fluorinated enamine intermediates.