title: Metal-free α-CH amination of ethers with hypervalent sulfonylimino-λ3-bromane that acts as an active nitrenoid.
abstract: Hypervalent N-triflylimino-λ(3)-bromane undergoes direct and regioselective α-C-H amination of ethers at room temperature under transition metal-free conditions. Kinetic results, substituent and deuterium isotope effects suggest an asynchronous concerted organonitrenoid transition state with some hydride transfer character, analogous to that for alkane C-H insertions.
authors.affiliation: Graduate School of Pharmaceutical Sciences, University of Tokushima, 1-78 Shomachi, Tokushima 770-8505, Japan. mochiai@ph.tokushima-u.ac.jp
authors.forename: Masahito
authors.initials: M
authors.lastname: Ochiai
authors.forename: Shinichi
authors.initials: S
authors.lastname: Yamane
authors.forename: Md Mahbubul
authors.initials: MM
authors.lastname: Hoque
authors.forename: Motomichi
authors.initials: M
authors.lastname: Saito
authors.forename: Kazunori
authors.initials: K
authors.lastname: Miyamoto
mesh_terms: D000586:Amination; D001969:Bromobenzenes / Q000737:chemistry*; D002244:Carbon / Q000737:chemistry; D003903:Deuterium / Q000737:chemistry; D004987:Ethers / Q000737:chemistry*; D006859:Hydrogen / Q000737:chemistry; D007097:Imines / Q000737:chemistry*; D007700:Kinetics; D008698:Mesylates / Q000737:chemistry*; D008670:Metals / Q000737:chemistry; D013237:Stereoisomerism; D013696:Temperature
chemical_list: D001969:Bromobenzenes; D004987:Ethers; D007097:Imines; D008698:Mesylates; D008670:Metals; D002244:Carbon; D006859:Hydrogen; D003903:Deuterium