title: Alkene diamination using electron-rich amines: hypervalent iodine-promoted inter-/intramolecular C-N bond formation.
abstract: A combined inter-/intramolecular oxidative diamination of terminal alkenes is described that uses a hypervalent iodine oxidant and a nucleophilic amine to produce 3-aminoindolines at room temperature. This operationally straightforward and metal-free protocol is compatible with a broad range of functional groups. A mechanism involving the conversion of the amine to an electrophilic nitrogen source is advanced and used to identify a protocol effective with substoichiometric amounts of iodide and commercially available phenyl iodobenzene diacetate (PIDA) as the stoichiometric oxidant.
authors: Department of Chemistry and Vanderbilt Institute of Chemical Biology, Vanderbilt University , Nashville, Tennessee 37235, United States.
authors: Ki Bum
authors: KB
authors: Hong
authors: Jeffrey N
authors: JN
authors: Johnston
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D000588:Amines / Q000138:chemical synthesis* / Q000737:chemistry*; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D007455:Iodine / Q000737:chemistry; D015394:Molecular Structure; D010084:Oxidation-Reduction
chemical_list: D000475:Alkenes; D000588:Amines; D007455:Iodine