Chelating hemilabile ligands are of interest for applications in organometallic catalysis. In this respect, N-benzotriazolyl and N-pyrazolyl derivatives have been previously studied as potential metal chelates. In this study, the reaction of benzotriazole and methyl acrylate without solvent or catalyst resulted in an isomeric mixture of N-benzotriazolylpropanoate derivatives (L1, L2) in high yields by a Michael addition. An analogous reaction of 3,5-dimethylpyrazole and methyl acrylate produced an N-pyrazolylpropanoate derivative (L3). The reactions of L1, L2, L3, and a previously prepared N-benzotriazolylpropanamide derivative (L4, L5) with RuCl2(PPh3)3 and (COD)RuCl2 were investigated by IR and NMR spectroscopy. Reactions of L1 with RuCl2(PPh3)3 yielded a red/orange precipitate assigned to a Ru complex in which the ligand binds in a bidentate fashion. 31P NMR studies indicated that the complex transitions into a bridged structure in solution. Reactions of L3 with (COD)PdCl2 initially yielded a monodentate trans complex that isomerizes reversibly to the cis isomer. The kinetics of the isomerization was analyzed using NMR spectroscopy.

Synthesis of N-benzotriazolyl and N-pyrazolyl derivatives as chelating ligands for ruthenium and palladium complexes

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