Self-assembly of structurally diverse diaminocarbene ligands at metal centers

INOR 122

Yoshitha A. Wanniarachchi, y_anju@yahoo.com, Yuri Kogiso, kogiso@okstate.edu, and LeGrande M. Slaughter, lms@chem.okstate.edu. Department of Chemistry, Oklahoma State University, Physical Science I, Stillwater, OK 74078-3071
Diaminocarbenes are among the most potent σ-donor ligands available for binding to transition metals. We have investigated the nucleophilic addition of amines to metal-bound isocyanides as a versatile synthetic route to new diaminocarbene complexes of late transition metals for use in catalysis and other applications. Judicious electronic tuning of the isocyanide substituents has been found to promote self-assembly of a variety of chelated bis(carbene) late metal complexes from structurally diverse diamine precursors, including chiral examples. The stabilities of the resulting complexes as a function of chelate ring size have been investigated. For example, a chelated bis(carbene) palladium complex with a 5-membered chelate ring exhibits reversible ring opening to form a monocarbene-isocyanide complex, and a van't Hoff analysis of this equilibrium allowed interrogation of the metal-carbene bond energetics. Larger chelate rings showed greatly enhanced stability and suitability for catalysis. Evaluations of the σ-donor abilities of the carbene ligands will be reported.