四氟苯并 BODIPY：BODIPY 染料衍生物区域选择性合成的平台。
Tetrafluorobenzo-Fused BODIPY: A Platform for Regioselective Synthesis of BODIPY Dye Derivatives.
机构信息
Dipartimento di Scienze e Tecnologie Chimiche , University of Rome Tor Vergata , Via della Ricerca Scientifica 1 , 00133 Rome , Italy.
Department of Chemistry , Louisiana State University , Baton Rouge , Louisiana 70803 , United States.
出版信息
J Org Chem. 2018 Jun 15;83(12):6498-6507. doi: 10.1021/acs.joc.8b00789. Epub 2018 May 29.
Abstract
A novel route for the synthesis of unsymmetrical benzo-fused BODIPYs is reported using 4,5,6,7-tetrafluoroisoindole as a precursor. The reactivity of the 3,5-dibromo tetrafluorobenzo-fused BODIPY was investigated under nucleophilic substitution and Pd(0)-catalyzed cross-coupling reaction conditions. In addition to the 3,5-bromines, one α-fluoro group on the benzo-fused ring can also be functionalized, and an unusual homocoupling with formation of a bisBODIPY was observed. This new class of fluorinated BODIPYs could find various applications in medicine and materials.
摘要
本文报道了一种利用 4,5,6,7-四氟异吲哚作为前体合成不对称苯并稠合 BODIPY 的新方法。研究了 3,5-二溴四氟苯并稠合 BODIPY 在亲核取代和 Pd(0)-催化交叉偶联反应条件下的反应性。除了 3,5-溴之外，苯并稠合环上的一个α-氟也可以进行官能化，并且观察到不寻常的同偶联反应，形成双 BODIPY。这类新型氟化 BODIPY 在医学和材料领域可能有广泛的应用。
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