通过基于磷的GAP协议对缺电子烯烃进行区域和非对映选择性的邻位氨基溴化反应。
Regio- and Diastereoselective Vicinal Aminobromination of Electron Deficient Olefins via Phosphorus-Based GAP Protocol.
作者信息
Rahman Anis Ur, Zarshad Nighat, Khan Iltaf, Faiz Faisal, Li Guigen, Ali Asad
机构信息
Institute of Chemistry and BioMedical Sciences, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, China.
School of Chemistry and Chemical Engineering, Southeast University, Nanjing, China.
出版信息
Front Chem. 2021 Sep 8;9:742399. doi: 10.3389/fchem.2021.742399. eCollection 2021.
Chemical synthesis based on Group-Assisted Purification chemistry (GAP) has been prolifically used as a powerful, greener and ecofriendly tool so far. Herein, we report hypervalent iodine (III) mediated regio- and diastereoselective aminobromination of electron-deficient olefins using group-assisted purification (GAP) method. By simply mixing the GAP auxiliary-anchored substrates with TsNH-NBS as nitrogen/bromine sources and PhI(OAc) as a catalyst, a series of vicinal bromoamines with multifunctionalities were obtained in moderate to excellent yields (53-94%). The vicinal bromoamines were obtained without column chromatography and/or recrystallization simply by washing the crude mixtures with cosolvents and thus avoiding wastage of silica, solvents, time, and labor. The GAP auxiliary is recyclable and reusable.
迄今为止，基于基团辅助纯化化学（GAP）的化学合成已被广泛用作一种强大、更绿色且环保的工具。在此，我们报道了使用基团辅助纯化（GAP）方法，通过高价碘（III）介导缺电子烯烃的区域和非对映选择性氨基溴化反应。通过简单地将GAP辅助锚定的底物与作为氮/溴源的对甲苯磺酰胺 - N - 溴代琥珀酰亚胺（TsNH - NBS）以及作为催化剂的乙酸碘苯（PhI(OAc)）混合，以中等至优异的产率（53 - 94%）获得了一系列具有多种功能的邻位溴代胺。邻位溴代胺无需柱色谱和/或重结晶，只需用共溶剂洗涤粗混合物即可获得，从而避免了硅胶、溶剂、时间和人力的浪费。GAP辅助剂可回收再利用。
Zotero 插件