Cycloisomerization of a dienyne-mediated by (NHC)Au(I) (NHC = N-heterocyclic carbene) complexes

ORGN 360

Nicolas Marion, nmarion@uno.edu1, Pierre de Frémont, megapape@yahoo.fr1, Natalie M. Scott1, Edwin D. Stevens, estevens@uno.edu1, and Steven P. Nolan, snolan@iciq.es2. (1) Chemistry Department, University of New Orleans, 2000 Lakeshore Dr, New Orleans, LA 70148, (2) Nolan group, Institut of Chemical Research of Catalonia (ICIQ), Av. Països Catalans, 16, 43007 Tarragona, Spain
Use of NHC (N-heterocyclic carbene) in Au(I)-catalyzed cycloisomerization of enyne results in the formation of a new type of product. Varying the substituents on the NHC ligand bound to gold has allowed for fine tuning the distribution of bicyclo[n.1.0] derivatives. The influence of silver salt additives, solvent and temperature has been examined. Based on these results and related experiments, a proposed mechanism leading to the formation of the three bicyclic products is presented.

 

Metal-Mediated Reactions and Syntheses
1:00 PM-5:00 PM, Tuesday, 30 August 2005 Washington DC Convention Center -- 202B, Oral

Division of Organic Chemistry

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