Metal-free C-H amination of unactivated hydrocarbons with sulfonylimino-λ3-bromanes generated in situ from (diacetoxybromo)benzene

A simple method for direct metal-free C-H amination of unactivated hydrocarbons using easy-handling diacetoxy-lambda(3)-bromane and triflylamide or sulfamate esters was developed. The high 2 degrees/3 degrees regio-selectivities and deuterium isotope effects suggest a concerted organonitrenoid transition state, analogous to C-H amination with N-triflylimino-lambda(3)-bromane.