Transition-metal carbene complexes have become highly studied organometallic species because of their potential use for catalytic applications. Previous studies of complexes featuring an indenediide backbone have been found to be successful in catalyzing the cycloisomerization of lactams through metal/ligand cooperative catalysis. The focus of our group has been in organometallic complexes featuring a methanediide backbone, which lacks the conjugated system of the indenediide backbone but may offer greater versatility in terms of functional groups it can cyclize. Previously isolated complexes feature platinum(II) or palladium(II) metal centers and triphenylphosphine as a neutral ligand but the triphenylphosphine ligand seems to coordinate too strongly to the metal center for the complex to be effective as a catalyst. In this report are the preliminary results for the synthesis of new palladium complexes featuring the aforementioned bis(diphenylthiophosphinoyl)methanediide ligand utilizing several palladium(II) precursors featuring poorly coordinating neutral ligands including 1,5-cyclooctadiene, acetonitrile, and benzonitrile. In addition, results for a substrate test on both the previously synthesized platinum(II) and palladium(II) complexes, using methylene chloride and THF as solvents, are presented. The results found in the substrate test can be used to characterize the basicity of the methandiide carbon to aid in diversifying the substrate scope.

Synthesis of new bis(diphenylthiophosphinoyl)methanediide palladium(II) complexes

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

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