Iron-Catalyzed Alkyne-Carbonyl Metathesis for the Synthesis of 6,7-Dihydro-5H-dibenzo[c,e]azonines

The synthesis of nine-membered rings via alkyne-carbonyl metathesis is reported. The alkyne and acetal units contained in a biaryl substrate undergo the intramolecular alkyne-carbonyl metathesis reaction under FeCl3-catalysis to furnish the unexplored 6,7-dihydro-5H-dibenzo[c,e]azonines. The method provides an alternative to existing routes to nine-membered rings with cheap, non-toxic iron catalysts and milder conditions.