Abstract:
A metal and base free synthesis of primary amines has been developed at ambient temperature through
ipso amination of diversely functionalized organoboronic acids, employing a combination of [bis(trifluoroacetoxy)iodo]benzene (PIFA)–N-bromosuccinimide (NBS) and methoxyamine hydrochloride as the
aminating reagent. The amines were primarily obtained as their trifluoroacetate salts which on subsequent
aqueous alkaline work up provided the corresponding free amines. The combination of PIFA–NBS is
found to be the mildest choice compared to the commonly used strong bases (e.g. n-BuLi, Cs2CO3) for
activating the aminating agent. The reaction is expected to proceed via activation of the aminating
reagent followed by B–N 1,2-aryl migration.
