Transition metal-free C-F/C-Cl/C-C cleavage of ClCF2COONa for the synthesis of heterocycles

Abstract

A transition metal-free and external oxidant-free annulation of substrates having two nitrogen-nucleophilic sites with ClCF₂COONa was demonstrated, affording a series of 1,3,5-triazines and quinazolinones in up to 96% yields. Notably, ClCF₂COONa was employed as the C1 synthon for valuable heterocycles. Using this protocol, two C-N bonds were formed in one pot via the cleavage of two C-F bonds, one C-Cl bond and one C-C bond. This method avoided the use of a transition metal and an oxidant and generated low toxicity inorganic waste.