title: Metal-free C-H amination of unactivated hydrocarbons with sulfonylimino-λ(3)-bromanes generated in situ from (diacetoxybromo)benzene.
abstract: A simple method for direct metal-free C-H amination of unactivated hydrocarbons using easy-handling diacetoxy-λ(3)-bromane and triflylamide or sulfamate esters was developed. The high 2°/3° regioselectivities and deuterium isotope effects suggest a concerted organonitrenoid transition state, analogous to C-H amination with N-triflylimino-λ(3)-bromane.
authors.affiliation: Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-12 Hongo, Bunkyo-ku, Tokyo, 113-0033, Japan. kmiya@mol.f.u-tokyo.ac.jp.
authors.forename: Kazunori
authors.initials: K
authors.lastname: Miyamoto
authors.forename: Taiga
authors.initials: T
authors.lastname: Ota
authors.forename: Md Mahbubul
authors.initials: MM
authors.lastname: Hoque
authors.forename: Masahito
authors.initials: M
authors.lastname: Ochiai
mesh_terms: D000586:Amination; D000588:Amines / Q000138:chemical synthesis* / Q000737:chemistry; D001969:Bromobenzenes / Q000737:chemistry*; D006838:Hydrocarbons / Q000737:chemistry*; D007097:Imines / Q000737:chemistry*; D015394:Molecular Structure; D009861:Onium Compounds / Q000737:chemistry*; D013450:Sulfones / Q000737:chemistry*
chemical_list: D000588:Amines; D001969:Bromobenzenes; D006838:Hydrocarbons; D007097:Imines; D009861:Onium Compounds; D013450:Sulfones; C540083:sulfonylimino-lambda3-bromane