Breaking aromatic rings apart

Aromatic rings are incredibly strong and stable, owing to their aromaticity and delocalized electron density shared around the ring. Breaking them apart selectively is therefore typically possible only under forcing conditions. Here, Ning Jiao and colleagues report a copper-catalysed process that opens up commmon aromatics such as anilines, aryl boronic acids and aryl halides into acylic vinyl nitriles, in the presence of sodium azide. This reactivity could enable aromatics to be used as chemical feedstocks in ways that are currently not possible, and is briefly demonstrated by the synthesis of adipic acid derivatives, which form the backbone of nylon. The approach holds promise in upgrading biomass and petroleum-derived feedstocks.