AUTHOR=Rahman Anis Ur , Zarshad Nighat , Khan Iltaf , Faiz Faisal , Li Guigen , Ali Asad TITLE=Regio- and Diastereoselective Vicinal Aminobromination of Electron Deficient Olefins via Phosphorus-Based GAP Protocol JOURNAL=Frontiers in Chemistry VOLUME=9 YEAR=2021 URL=https://www.frontiersin.org/journals/chemistry/articles/10.3389/fchem.2021.742399 DOI=10.3389/fchem.2021.742399 ISSN=2296-2646 ABSTRACT=

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 TsNH2–NBS as nitrogen/bromine sources and PhI(OAc)2 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.