Au(I)-Catalyzed formation of indenes vs. conjugated enones from benzylpropargyl acetate: A water-sensitive reaction

ORGN 455

Nicolas Marion, nmarion@uno.edu1, Ronan Gealageas1, 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
Benzylpropargyl acetates were reacted with in situ generated cationic gold(I) complexes. As a function of reaction conditions, formation of indenes or conjugated enones was observed. The substitution on the aryl and at the propargylic and acetylenic positions as well as the influence of the NHC ligand (NHC = N-heterocyclic carbene) bound to gold were examined. A mechanistic pathway accounting for both transformations is proposed.

 

Modern Acetylene Chemistry
8:00 PM-10:00 PM, Tuesday, 12 September 2006 Moscone Center -- Hall D, Poster

Division of Organic Chemistry

The 232nd ACS National Meeting, San Francisco, CA, September 10-14, 2006