Copper-Catalyzed Annulation-Trifluoromethyl Functionalization of Enynones

The Cu(I)-catalyzed annulation-halotrifluoromethylation and cyanotrifluoromethylation of enynones have been established, enabling multibond formations of the synthesis of quaternary carboncentered 1-indanones in moderate to good chemical yields. The reaction of enynones with Togni's reagent and chloro- or bromotrimethylsilane afforded halo- and CF3-containing 1-indenones. However, the addition of K3PO4 as a base into the catalytic system led to forming cyano-anchored (Z)-1-indanones as major stereoisomeric products. This strategy exhibits remarkable compatibility with a wide range of enynones.

Automated summary

The Cu(I)-catalyzed annulation-halotrifluoromethylation and cyanotrifluoromethylation of enynones have been successfully developed, allowing for the construction of quaternary carbon-centered 1-indanones through multibond formations with moderate to good chemical yields. The reaction of enynones with Togni's reagent and chloro- or bromotrimethylsilane yielded halo- and CF3-containing 1-indenones, while the addition of K3PO4 as a base resulted in the formation of cyano-anchored (Z)-1-indanones as the major stereoisomeric products. This strategy exhibits excellent compatibility with a wide range of enynones.