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Efficient Synthesis of Fluoroalkylated Imidazoles via a Metal‐Free Cascade Michael Addition/Azidation/Cycloamination Process
Author(s) -
Wu Jun,
Zhang Hui,
Ding Xiao,
Tan Xuefei,
Shen Hong C.,
Chen Jie,
He Weimin,
Deng Hongmei,
Song Liping,
Cao Weiguo
Publication year - 2018
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201801310
Subject(s) - chemistry , michael reaction , sodium azide , azide , cascade , reagent , combinatorial chemistry , organic chemistry , catalysis , chromatography
In the presence of KI and (diacetoxyiodo)benzene (PIDA), primary amines bearing an α‐hydrogen can be efficiently converted to fluoroalkylated imidazoles by reacting with fluoroalkylated alkynes and sodium azide via a cascade Michael addition/azidation/cycloamination process. KI plays a crucial role in this reaction by generating iodine(I) species to promote the cyclization. Substrate scope was explored, and the application of this protocol was demonstrated. Additionally, a plausible reaction mechanism was proposed.