Polycyclic heteroaromatics via hydrazine-catalyzed ring-closing carbonyl-olefin metathesis

The use of hydrazine-catalyzed ring-closing carbonyl-olefin metathesis (RCCOM) to synthesize polycyclic heteroaromatic (PHA) compounds is described. In particular, substrates bearing Lewis basic functionalities such as pyridine rings and amines, which strongly inhibit acid catalyzed RCCOM reactions, are shown to be compatible with this reaction. Using 5 mol% catalyst loadings, a variety of PHA structures can be synthesized from biaryl alkenyl aldehydes, which themselves are readily prepared by cross-coupling.

Automated summary

The use of hydrazine-catalyzed ring-closing carbonyl-olefin metathesis (RCCOM) to synthesize polycyclic heteroaromatic (PHA) compounds is described in this article. It is shown that substrates containing Lewis basic functionalities such as pyridine rings and amines, which inhibit acid catalyzed RCCOM reactions, are compatible with this reaction. By using a catalyst loading of 5 mol%, a variety of PHA structures can be synthesized from biaryl alkenyl aldehydes prepared by cross-coupling.