Oxidative cross-coupling of nucleophiles via Pd(I), and other tales
Organic and Biological Seminar Series Abstract: Palladium catalyzed cross coupling reactions are typically associated with a Pd(0)/Pd(II) redox couple. The use of Pd(I) in catalysis has been limited to presumed intermediates (1), and Pd-Pd dimers (2). Following the recent isolation of a stable, monomeric Pd(I) species,1 we report the use of this complex in the oxidative cross-coupling of aryl-boron and aryl-antimony nucleophiles, via a proposed Pd(0)/(I)/(II) redox cycle (3). This reaction tolerates a wide variety of substrates, with >20:1 selectivity for cross coupled products. This strategy offers a new approach to achieving the selective cross-coupling of nucleophiles and offers insight into the novel reactivity of Pd(I).
Dr Joel Hooper, Monash University