4.6 Article

TBAX/Oxone-Mediated Halogenation of Pyrazoles and Other Heterocycles: An Entry to Important Cross-Coupling Reactions

期刊

CHEMISTRY-AN ASIAN JOURNAL
卷 17, 期 22, 页码 -

出版社

WILEY-V C H VERLAG GMBH
DOI: 10.1002/asia.202200778

关键词

Halogenation; TBAX; Pyrazoles; Microwave; Heterocycles

资金

  1. CSIR-India [HCP-23]

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A facile and eco-friendly halogenation protocol using TBAX as halogenating agent has been developed, showing great potential in organic synthesis and demonstrating its applicability in laboratory research.
A facile, sustainable and eco-friendly protocol has been developed for the halogenation of various heterocycles using TBAX (TBAI/TBAB/TBACl) as halogenating agent, which afforded the products in 90-95% isolated yields. The reaction proceeds with low-cost TBAX and uses greener conditions like EtOH as a solvent and microwave as an alternative energy source for reaction. This protocol has been applied on pyrazoles and extended to different heterocycles like 7-azaindole, indazole, indole and 2-phenylimidazo[1,2-alpha]pyridines. The gram-scale iodination reaction has also been successfully performed by optimizing conventional heating conditions, which demonstrates its potential applicability in organic synthesis. Further these halogenated pyrazoles have been utilized for different coupling reactions including formation of arylated, alkynylated and sulfenated pyrazoles. However, TBAF mediated fluorination did not work.

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