Nickel(0) mediated oxidative coupling of carbon dioxide and imines

CHED 274

Laura Sinault, Alexandre Graet, and Marc M. Baum, m.baum@oak-crest.org. Department of Chemistry, Oak Crest Institute of Science, 2275 E. Foothill Blvd., Pasadena, CA 91107
Nickel(0) complexes are known to react with imines in the presence of CO2 to form five-membered nickelacycles. The long-term aim of our research is to obtain highly functionalized heterocycles from such nickelacycles via Ni-C insertion reactions, followed by reductive elimination. During the course of these investigations, we discovered that imines can be coupled with amines/aldehydes in the presence of Ni(0), CO2, and a Lewis acid to produce useful 5-membered heterocycles (e.g., imidazolidine and/or triazolidine derivatives). We have already shown that CO2 and the Lewis acid play an important role in this novel chemistry.