Regio- and Diastereoselective Vicinal Aminobromination of Electron Deficient Olefins via Phosphorus-Based GAP Protocol

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.

Updates on hypervalent-iodine reagents: metal-free functionalisation of alkenes, alkynes and heterocycles

“…The products obtained were easily purified and the GAP auxiliaries were recycled and reused after every reaction (Scheme 15). 64…”

“…The products obtained were easily purified and the GAP auxiliaries were recycled and reused after every reaction (Scheme 15). 64 In the last few years, HVI(III)-mediated oxidative fluorination of olefins has emerged as an excellent method for the introduction of the fluoro-group into organic moieties. Utilising this strategy, many researchers have reported various methods for the introduction of fluorine moieties into the alkene system.…”

A critical review on metal-organic frameworks (MOFs) based nanomaterials for biomedical applications: Designing, recent trends, challenges, and prospects

“…Around two million people die from viral infections each year. Vaccination is a typical approach to preventing viral infections, however, there are currently ineffective vaccinations for many viral infections [ 172 ]. To overcome this problem, MOFs have been introduced that have the potential to improve the antiviral therapeutic system.…”