Zeolites catalyze the halogen exchange reaction of alkyl halides

Simple aluminosilicates, including NaX and NaY zeolites, catalyze the selective halogen exchange reaction between two different alkyl organohalides, either in batch or in flow, without any additive or solvent, by simply heating at 130 degrees C and with <5 wt% of solid catalyst. The reaction protocol tolerates different functional groups and gives two new organohalides in good yields. Mechanistic studies unveil the key role of the zeolite oxygen atoms and countercations, to trigger the heterolytic scission of the R-X bond and generate intermediate alkoxy and halide species, respectively, which recombine within the zeolite framework. These results open a new way to synthesize organohalides with simple solid catalysts and expand the use of aluminosilicates in organic synthesis.

Automated summary

Simple aluminosilicates, such as NaX and NaY zeolites, can catalyze the selective halogen exchange reaction between different alkyl organohalides without any additives or solvents. By heating at 130 degrees C with a small amount of solid catalyst, new organohalides are produced in good yields, tolerating different functional groups. Mechanistic studies reveal the importance of zeolite oxygen atoms and countercations in facilitating the reaction.