Perfluoroalkylations and perfluorooxaalkylations. Part 3. Chloro-substituted diazines as substrates in copper-mediated cross-coupling

Article abstract of DOI:10.1016/0022-1139(94)03205-E

The (perfluoroalkyl)- and (perfluorooxaalkyl)diazines, 2,4-bis(perfluorooctyl)pyrimidine (3), 2,4,6-tris(perfluorooctyl)pyrimidine (6a), 2,4,6-tris(perfluoro-6-methyl-5-oxaheptyl)pyrimidine (6b), 3,6-bis(perfluorooctyl)pyridazine (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. - Keywords: Perfluoroalkylations; Perfluorooxaalkylations; Chloro-substituted diazines; Cross-coupling; NMR spectroscopy; Mass spectrometry