Journal of Organometallic Chemistry p. 1057 - 1063 (2004)
Update date:2022-08-03
Topics:
Ionkin, Alex S.
Marshall, William J.
A set of isomeric para- and meta-trimethylsilylphenyl ortho -substituted N, N-phenyl α-diimine ligands [(Ar-N=C(Me) -(Me)C=N-Ar) Ar=2,6-di(4-trimethylsilylphenyl)phenyl (16); Ar=2,6-di(3-trimethylsilylphenyl)phenyl (17)] have been synthesized through a two-step procedure. The palladium-catalysed cross-coupling reaction between 2,6-dibromophenylamine (7) and 4-trimethylsilylphenylboronic acid (8), 3-trimethylsilylphenylboronic acid (9) was used to prepare 4,4′-bis(trimethylsilyl) -[1,1′;3′,1″]terphenyl-2 ′-ylamine (10) and 3,3′-bis (trimethylsilyl)-[1,1′;3′, 1″] terphenyl-2′-ylamine (11). The di-1-adamantylphosphine oxide Ad2P(O)H (13) and di-tert-butyl-trimethylsilylanylmethylphosphine tert-Bu2 P-CH2-SiMe3 (14) were used for the first time as ligands for the Suzuki coupling. The condensation of 2,2,3,3-tetramethoxybutane (15) with anilines 10 and 11 afforded α-diimines 16 and 17. The reaction of π-allylnickel chloride dimer (18), α-diimines (16), (17) and sodium tetrakis[3,5-bis (trifluoromethyl)phenyl]borate (BAF) (19) or silver hexafluoroantimonate (20) led to two sets of isomeric complexes [η3-allyl (Ar-N=C(Me)-(Me)C=N-Ar)Ni]+ X-, [Ar=2,6-di(4-trimethylsilylphenyl)phenyl, X=BAF (3), X=SbF6 (4); Ar=2,6-di(3-trimethylsilylphenyl)phenyl, X=BAF (5), X=SbF6 (6)]. The steric repulsion of closely positioned trimethylsilyl groups in 4 caused the distortion of the nickel square planar coordination by 17.6° according to X-ray analysis.
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