Dual Role of N‐Bromosuccinimide as Oxidant and Succinimide Surrogate in Domino One‐Pot Oxidative Amination of Benzyl Alcohols for the Synthesis of α–Imido Ketones

A transition‐metal‐free oxidative amination of secondary benzyl alcohols has been developed using N ‐bromosuccinimide as the oxidant and source of succinimide. The control experiments revealed that the transformation underwent via oxidation of alcohol to ketone, α‐bromination of ketone and diazabicyclo[5.4.1]undec‐7‐ene (DBU) base‐mediated nucleophilic substitution of the by‐product succinimide. Various substituted benzyl alcohols and N ‐bromoimides were examined to form α‐imido ketones in short reaction timespans. The protocol was successfully extended to a gram scale reaction.