期刊
TETRAHEDRON
卷 76, 期 17, 页码 -出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2020.131113
关键词
BODIPY; Chlorination; Oxidative nucleophilic substitution of hydrogen; ONSH
资金
- Newcastle University (NCL)
- Shaqra University
- EPSRC for X-ray crystallography facilities at NCL [EP/F03637X/1]
- EPSRC UK National Mass Spectrometry Facility at Swansea University
- EPSRC [EP/F03637X/1] Funding Source: UKRI
Regioselective halogenation is often a key step in the formation of substituted 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY) fluorophores, through the enablement of subsequent downstream C-C or C-X bond forming steps via SNAr or metal catalyzed cross-coupling reactions. Classical SEAr halogenation of unsubstituted BODIPYs results in 2/6-substitution, precluding easy access to 3/5-halogenated BODIPYs. Herein we present our development of a 3,5-dihalogenation reaction of unsubstituted BODIPYs, via a double oxidative nucleophilic substitution of hydrogen with chloride. Reaction of a range of meso-aryl, but otherwise unsubstituted, BODIPYs with stoichiometric Cu(OTf)(2) in the presence of ethanolamine and tetrabutylammonium chloride gives high isolated yields of the corresponding 3,5-dichlorinated BODIPYs, facilitating access to these valuable synthetic intermediates. (C) 2020 Elsevier Ltd. All rights reserved.
作者
我是这篇论文的作者
点击您的名字以认领此论文并将其添加到您的个人资料中。
推荐
暂无数据