Priced to Sell. New Recyclable Reagents for Catalysis of Heterogeneous Cross-Couplings.
Bruce H. Lipshutz,* Zarko Boskovic, Tom Butler, Danielle Nihan, Elizabeth Swift, and Ben Taft

Nickel and copper are base metals within groups 10 and 11, respectively, and are among the late transition metals that do most of the cross-couplings in organic synthesis.  Both have been previously independently impregnated into a charcoal matrix and subsequently shown to catalyze various bond constructions under heterogeneous conditions. New chemistry of nickel mounted between the sheets of graphite (Ni/C_g) will briefly be discussed as it relates to several ‘name’ reactions, along with comparisons between this catalyst and the corresponding reagent in charcoal (Ni/C).  A new reagent (“Cu + Ni/C”) will also be disclosed, representing the first known example of a heterogeneous catalyst that contains two metals within the charcoal pores that can be used independently or in harmony.  This recyclable species mediates cross-couplings characteristic of group 10 or group 11 metals, or tandem reactions where the presence of both are useful.  Microwave assistance is the key tool in this chemistry.