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α-Halo-N-tosylhydrazones are employed as reagents for the formation of multiple carbon–carbon bonds in the three-component reactions. In this transformation, a strategy has been designed to generate the diazo intermediate by using a nucleophile to react with the azoalkene intermediate generated in situ from the α-halo-N-tosylhydrazone. The diazo intermediate thus generated further undergoes transition-metal-free C–C bond forming reaction with arylboronic acids.

The title scalable reaction proceeds via diazotation and metal-free coupling of the resulting diazo esters or nitriles with arylboronic acids.

By employing different reaction conditions, both (2,2,2-trifluoroethyl)arenes and gem-difluorovinylarenes are accessible.

The title reaction is developed as a new mild and straightforward method to prepare various trifluoromethylated alkenes and dienes.

A new method for the direct synthesis of aromatic nitriles from the corresponding methyl arenes is presented using tert-butyl nitrite as the nitrogen source and oxidant in the presence of Pd(OAc)2 and N-hydroxyphthalimide catalysts.