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R4NHal/NOHSO4: A Usable System for Halogenation of Isoxazoles, Pyrazoles, and Beyond.

Oksana B BondarenkoGeorgy L KaretnikovArseniy I KomarovAleksandr I PavlovSvetlana N Nikolaeva
Published in: The Journal of organic chemistry (2020)
A new convenient and versatile halogenating system (R4NHal/NOHSO4), giving straightforward and general access to halogenated 3,5-diaryl- and alkylarylisoxazoles, pyrazoles and electron-rich benzenes from the corresponding scaffolds, is suggested. The method provides excellent regioselectivity, scalability to the gram scale, and a broad scope for both aromatics and halogens. A three-step, one-pot reaction protocol was developed, and a series of 3,5-diaryl-4-haloisoxazoles has been efficiently synthesized from 1,2-diarylcyclopropanes under suggested nitrosating-halogenating conditions.
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