Pd(COD)(DQ): A Stable, Versatile, and Monometallic Palladium(0) Source for Organometallic Synthesis and Catalysis

Pd(COD)(DQ) (COD=1,5-cyclooctadiene, DQ=duroquinone) is a robust, air-stable, and well-defined 18-electron Pd(0)–olefin complex first synthesized by Sakai et al. in 1983. Herein, we describe an operationally convenient synthetic procedure to prepare this complex on decagram scale; we show that it undergoes facile ligand exchange with phosphines, N-heterocyclic carbenes, and other catalytically important ancillary ligands to give stable organometallic products; and we demonstrate its catalytic competence in numerous useful reactions in organic synthesis. We anticipate that the pronounced stability of Pd(COD)(DQ) and its favorable handling properties will allow it to find use as a convenient Pd(0) source in academic and industrial research labs.