Efficient Synthesis of Fluoroalkylated Imidazoles via a Metal‐Free Cascade Michael Addition/Azidation/Cycloamination Process | Zendy

Wu Jun | Zendy; Zhang Hui | Zendy; Ding Xiao | Zendy; Tan Xuefei | Zendy; Shen Hong C. | Zendy; Chen Jie | Zendy; He Weimin | Zendy; Deng Hongmei | Zendy; Song Liping | Zendy; Cao Weiguo | Zendy

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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.

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