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

Anis Ur Rahman, Nighat Zarshad, Iltaf Khan, Faisal Faiz, Guigen Li, Asad Ali

Research output: Contribution to journalArticlepeer-review

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.

Original languageEnglish
Article number742399
JournalFrontiers in Chemistry
Volume9
DOIs
StatePublished - Sep 8 2021

Keywords

  • aziridinium
  • diastereoselectivity
  • iodobenzene diacetate
  • nitrogen/halogen source
  • protecting groups

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