Metal-free α-CH amination of ethers with hypervalent sulfonylimino-λ3-bromane that acts as an active nitrenoid

Abstract

Hypervalent N-triflylimino-λ³-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.