Rhodium-catalyzed intramolecular difluoromethylenative dearomatization of phenols to yield azaspirocyclohexadienones containing all-carbon quaternary centers in good to excellent yields was developed. A variety of functional groups proved compatible with the transformation. This method could also be used for difluoromethylenative dearomatization of indoles. Preliminary mechanism studies suggest that a pure radical mechanism is not involved in this reaction.

A novel palladium-catalyzed synthesis of substituted 3-methylene-3H-indoles from readily accessible alkynylimines has been developed. A wide variety of 2-fluoroalkyl-3-methylene-3H-indoles were synthesized in moderate to good yields through this cascade carbopalladation/CH activation process. This reaction can also be expanded to non-fluorinated substrates.

Fluorinated alkynyl ketones react with hydrazine to give fluorinated pyrazols in good to excellent yields with Au(I) as catalyst. All the reactions were carried out at room temperature with excellent regioselectivity.

Novel tricyclic 4-(trifluoromethyl)-[1,2,3]triazolo[1,5-a]quinoxalines were readily prepared from N-(o-haloaryl)alkynylimines and sodium azide via copper(I)-catalyzed tandem reactions. This synthetic strategy provides an efficient way to access a library of novel heterocyclic compounds that are of interest in drug discovery.

2-Fluoromethylated quinolines were synthesized through the reaction of N-aryl-fluorinated imidoyl iodides with terminal alkynes in good yields by the catalysis of copper(I) iodide (CuI) alone.

The 1,3-dipolar cycloaddition of fluoroalkylazides with electron deficient olefins was studied. A series of fluoroalkylated triazoline and pyrazolines were synthesized by this method. A ring opening and diazo intermediate mechanism was proposed.