PERFLUOROALKYLATIONS AND PERFLUOROOXAALKYLATIONS .3. CHLOROSUBSTITUTED DIAZINES AS SUBSTRATES IN COPPER-MEDIATED CROSS-COUPLING

The (perfluoroalkyl)- and (perfluorooxaalkyl)diazines, 2,4-bis(perfluorooctyI)pyrimidine (3), 2,4,6-tris(perfluorooctyl)pyrimidine (6a), 2,4,6-tris(perpuoro-6-methyl-5-oxaheptyl)pyrimidine (66), 3,6-bis(perfluorooctyl)pyridiazine (10) and 2,6-bis(perfluorooctyl)pyrazine (13), have been prepared in good yield. This was accomplished by using chloro-substituted diazines as substrates in copper-mediated cross-coupling reactions with perfluoroalkyl and perfluorooxaalkyl iodides. The yields of the cross-coupled products are influenced by the reaction conditions as well as by the structure of the fluoroaliphatic iodides and substrates.