Synthesis of Benzonitrile from Dinitrogen

The rhenium mediated synthesis of benzonitrile is reported with direct use of N-2 as a nitrogen source. The reaction affords benzonitrile in about 30% overall yield upon N-2 splitting and benzylation of resulting terminal nitride. Subsequent oxidation of an intermediate phenylketimido compound restores the parent rhenium complex within a full four-step synthetic cycle. The reaction shows that previously observed nitrile tautomerization is not a prerequisite for nitrile synthesis from N-2 with this system.