Yang Youjun, Escobedo Jorge O, Wong Alexander, Schowalter Corin M, Touchy Michael C, Jiao Lijuan, Crowe William E, Fronczek Frank R, Strongin Robert M
Department of Chemistry, Louisiana State University, Baton Rouge, LA 70803, USA.
J Org Chem. 2005 Aug 19;70(17):6907-12. doi: 10.1021/jo051002a.
A facile synthetic route utilizing readily available reagents affords a series of regioisomerically pure xanthene dye derivatives. Advantages include relatively mild conditions and good to excellent yields. Nonpolar, highly crystalline intermediates are isolable by standard chromatographic techniques. The intermediates are in the requisite xanthene oxidation state, thus avoiding the need for relatively inefficient oxidation chemistry and/or harsh conditions. During the course of this work, a new boron-mediated 1,2-aryl migration reaction was discovered.
利用易得试剂的简便合成路线可得到一系列区域异构体纯的呫吨染料衍生物。优点包括条件相对温和且产率良好至优异。非极性、高结晶性的中间体可通过标准色谱技术分离。这些中间体处于所需的呫吨氧化态，从而避免了相对低效的氧化化学方法和/或苛刻条件的需要。在这项工作过程中，发现了一种新的硼介导的1,2-芳基迁移反应。
