Abstract
New multidentate ligands have been synthesized by the condensation of 2‐(methylsulfanyl)benzoyl chloride with a range of amines bearing ancillary N or S donors. In reactions with PdCl2(NCPh)2, the ligands smoothly underwent direct cyclopalladation to give pincer complexes with 5,6‐ or 6,6‐membered fused metallocycles. The oxidation of the sulfide ligands with H2O2 afforded the corresponding sulfoxide derivatives, which readily formed analogous pincer complexes with the PdII ions. The realization of κ3‐S,N,X coordination (X = N or S) was confirmed by multinuclear NMR and IR spectroscopic data and, in some cases, X‐ray crystallography. An unusual dynamic behavior of the 6,6‐membered S,N,S complex with an organophosphorus ligand was additionally studied by the ROESY technique. All of the palladocycles obtained were tested as precatalysts for the Suzuki cross‐coupling of aryl bromides with arylboronic acids, which allowed us to evaluate the main structure–activity relationships.
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