Iron-Catalyzed Dearomatization of Biaryl Ynones with Aldehydes via Double C-H Functionalization in Eco-Benign Solvents: Highly Atom-Economical Synthesis of Acylated Spiro[5.5]trienones

The multiple C-H bonds of biaryl ynones render the 6-exo-trig regioselective C-H activation dearomatization to spiro[5.5]trienones challenging since the competing reactions of C-H bonds on Ar-1 or the ortho-C-H bonds on Ar-3 may result in 5-exo-trig cyclization to indenones or 6-exo-trig ortho-dearomatization, respectively. We here report an unprecendented dearomatization of biaryl ynones with aldehydes via double C-H functionalization where a regiospecific remote unactivated para-C-H functionalization of biaryl ynones efficiently furnishes acylated spiro[5.5]trienones. This cascade cyclization features a green catalyst and solvent and high atom- and step-economy.

Automated summary

The study presents an unprecedented dearomatization of biaryl ynones with aldehydes via double C-H functionalization, where regiospecific remote unactivated para-C-H functionalization efficiently furnishes acylated spiro[5.5]trienones, demonstrating high efficiency and economy.