Trialkyl borate assisted amination of fluorinated 1,3-diketones for synthesis of N,N′-1,2-phenylen-bis(β-aminoenones) and their Ni(II), Cu(II) and Pd(II) complexes

An effecient synthetic method for fluorinated tridentate β-aminoenones and tetradentate bis(β-aminoenones) via amination of fluorinated 1,3-diketones with o-phenylenediamine in the presence of trialkyl borates was developed. Ni(II), Cu(II) and Pd(II) complexes with tetradentate bis(β-aminoenones) were obtained. Their gaschromatographic behaviour and main fragmentation paths in the electron ionization mass spectra were described.

Graphical abstractFigure optionsDownload full-size imageDownload as PowerPoint slideHighlights► Trialkylborates hasten amination of fluorinated 1,3-diketones with o-phenylenediamine. ► Tributylborate promotes formation of fluorinated N,N′-1,2-phenylen-bis(β-aminoenones). ► Triethylborate assist to synthesis of fluorinated N-(2-aminophenyl)-β-aminoenones.