Using NBS Entirely: One-pot Tandem Synthesis of N-arylsuccinimides From Activated Arenes Under Microwave Irradiation

N-bromosuccinimide (NBS) is a versatile brominating reagent. It is used not only in radical bromination but also in electrophilic addition and electrophilic substitution reactions. NBS can be used to obtain aryl bromides, which are useful for further functionalization, such as coupling reactions for C/N/O/S-aryl bond formation. However, the succinimide group of NBS is poorly explored and is often treated as a waste. In this work, we propose the full use of NBS, both for bromination of arenes and for the incorporation of the succinimide group in a one-pot fashion. Using low-cost reagents such as Cu₂O and K₃PO₄, we were able to obtain N-arylsuccinimides in moderate to good yields directly from non-halogenated aromatics. It was observed that microwave irradiation was crucial to circumvent the low nucleophilicity of succinimide.