Revisiting the synthesis of aryl nitriles: a pivotal role of CAN

Facilitated by the dual role of Ceric Ammonium Nitrate (CAN), herein we report a cost-effective approach for the cyanation of aryl iodides/bromides with CAN-DMF as an addition to the existing pool of combined cyanation sources. In addition to being an oxidant, CAN acts as a source of nitrogen in our protocol. The reaction is catalyzed by a readily available Cu(ii) salt and the ability of CAN to generate ammonia in the reaction medium is utilized to eliminate the additional requirement of a nitrogen source, ligand, additive or toxic reagents. The mechanistic study suggests an evolution of CN- leading to the synthesis of a variety of aryl nitriles in moderate to good yields. The proposed mechanism is supported by a series of control reactions and labeling experiments.

Automated summary

The cost-effective cyanation of aryl iodides/bromides was achieved using CAN-DMF as a source of nitrogen, with Cu(II) salt as the catalyst. The mechanism involves an evolution of CN- leading to the synthesis of various aryl nitriles in moderate to good yields.