Hypervalent Iodine (III) Catalyzed Regio- and Diastereoselective Aminochlorination of Tailored Electron Deficient Olefins via GAP Chemistry

Anis Ur Rahman, Nighat Zarshad, Peng Zhou, Weitao Yang, Guigen Li, Asad Ali

Research output: Contribution to journalArticlepeer-review

Abstract

Herein, we report a protocol for highly efficient hypervalent iodine (III) mediated, group-assisted purification (GAP) method for the regioselectivities and stereoselective aminochlorination of electron-deficient olefins. A series of vicinal chloramines with multifunctionalities were acquired in moderate to excellent yields (45–94%), by merely mixing the GAP auxiliary-anchored substrates with dichloramine T and tosylamide as chlorine/nitrogen sources and iodobenzene diacetate as a catalyst. The vicinal chloramines were obtained without any column chromatographic purification and recrystallization simply by washing the reaction mixture with a minimum amount of common inexpensive solvents and thus avoiding wastage of silica, solvents, time, and labor. The GAP auxiliary is recyclable and reusable. This strategy is easy to handle, cost-effective, greener, sustainable, environmentally benign, and mostly suitable for the syntheses of vicinal haloamines from various electron-deficient alkenes.

Original languageEnglish
Article number523
JournalFrontiers in Chemistry
Volume8
DOIs
StatePublished - Jul 7 2020

Keywords

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

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