Department of Chemistry, M. V. Lomonosov Moscow State University, 119991 Moscow, Russian Federation.
J Org Chem. 2021 Jan 1;86(1):322-332. doi: 10.1021/acs.joc.0c02106. Epub 2020 Dec 21.
A new convenient and versatile halogenating system (RNHal/NOHSO), 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.
提出了一种新的方便且通用的卤化体系（RNHal/NOHSO），可从相应的骨架中直接、普遍地获得卤代 3,5-二芳基-和烷基芳基异恶唑、吡唑和富电子苯。该方法具有出色的区域选择性、可扩展性至克级规模，以及对芳烃和卤素的广泛适用性。开发了三步一锅反应方案，并在建议的亚硝化-卤化条件下，从 1,2-二芳基环丙烷高效合成了一系列 3,5-二芳基-4-卤代异恶唑。
