Nickel-catalyzed cycloaddition of alkynes and isocyanates

ORGN 389

Hung Duong and Janis Louie, louie@chem.utah.edu. Department of Chemistry, University of Utah, 315 South 1400 East, Salt Lake City, UT 84112-0850
Metal-catalyzed cycloaddition reactions represent a highly efficient and atom economical method to access heterocycles. For example, we discovered the combination of Ni and an appropriate ligand catalyzes the cycloaddition of alkynes and isocyanates to give pyridones. Employing bulky, N-heterocyclic carbene (NHC) ligands (such as 1,3-bis-(2,6-diisopropylphenyl)-4,5-dihydroimidazol-2-ylidene, SIPr) rather than phosphine ligands provided marked disparities in reactivity. Specifically, reaction conditions, product distribution, and pyridone regioselectivity differed between reactions. Mechanistic details of these processes will be discussed.
 

Bioorganic, Metal-Mediated Reactions, and Molecular Recognition
8:00 PM-10:00 PM, Tuesday, 30 August 2005 Washington DC Convention Center -- Hall A, Poster

Sci-Mix
8:00 PM-10:00 PM, Monday, 29 August 2005 Washington DC Convention Center -- Hall A, Sci-Mix

Division of Organic Chemistry

The 230th ACS National Meeting, in Washington, DC, Aug 28-Sept 1, 2005