1,1prime-Binaphthyl-2-methylpyridinium-based peroxophosphotungstate salts: synthesis, characterization, and their use as oxidation catalysts

2009

A series of 1,1′-binaphthyl-2-methylammonium and pyridinium salts 6, 7, and 8 was synthesized through the coupling reaction of 2-(bromomethyl)-1,1′-binaphthalene (5) with the dendritic tetraallyl pyridinedicarbinol dendron 2 as well as triethylamine and 4-tert-butylpyridine. Tetraallyl pyridinedicarbinol dendron 2 was prepared by allylation of commercially available diethyl pyridine-3,5-dicarboxylate (1). The allylation of 2 with allyltrimethylsilane in the presence of boron trifluoride was unsuccessful, as tetraallyl pyridinedicarbinol trifluoroboron adduct 3 was obtained instead of expected hexaallylpyridine compound 4. The catalytic hydrogenation of allyl groups of the ammonium salt of 2…