Rhodium-catalyzed cyclizations of pyridyl esters of 2-substituted phenylacetic acids

ORGN 78

Douglas B. Grotjahn, grotjahn@sundown.sdsu.edu, Department of Chemistry, San Diego State University, 5500 Campanile Drive, San Diego, CA 92182, Justin M. Hoerter, jhoerter@chem.wisc.edu, Department of Chemistry, University of Wisconsin-Madison, F Daniels and J H Mathews Chemistry Bldg, 1101 University Ave, Madison, WI 53706-1396, and Jeffrey L Gustafson, jlg0320@hotmail.com, Department of Chemistry and Biochemistry, San Diego State University, 5500 Campanile Drive, San Diego, CA 92182.
Various 2-substituted phenylacetic acids were made using Suzuki couplings. Their pyridyl esters (1) were used to investigate their rhodium(I)-catalyzed cyclization to napthols (4) or indene derivatives (5). The pathway to the cyclization products may include a ketene (2) or carbene (3) intermediate. Products 4 and 5 form in different ratios according to the ester used.

 

 

 

 

Heterocycles, Aromatics, Materials, Devices, Switches, Combinatorial Chemistry, Metal-Mediated Reactions
8:00 PM-10:00 PM, Sunday, 13 March 2005 Convention Center -- Hall D, Poster

Division of Organic Chemistry

The 229th ACS National Meeting, in San Diego, CA, March 13-17, 2005