ORGN 365 |
| Jiangtao Hao1, David A. Boyles1, and John T. Bendler2. (1) Department of Chemistry and Chemical Engineering, South Dakota School of Mines and Technology, 501 E. St. Joseph, Rapid City, SD 57701, (2) Physics Department, United States Naval Academy, 572 M Holloway Road, Michelson Hall, Annapolis, MD 21401 |
| New ether, ketone, and sulfone-linked biphenyl bisphenols were synthesized by Suzuki cross-coupling reactions of bis(4-bromophenyl)ether, bis(4-chlorophenyl)sulfone, and bis(4-chlorophenyl)ketone, respectively, with organoboron reagents, followed by the appropriate deprotection reaction. The Suzuki reaction of bis(4-bromophenyl) ether and that of bis(4-chlorophenyl)ketone with the organoboron reagent stopped at the unexpected mono-substituted Suzuki product. This result was attributed in part to the poor reactivity of aryl chlorides and bromides as well as to the low solubility of the monoarylated products in the solvent utilized. These difficulties were overcome by the use of new reactive organoboron reagents for Suzuki reaction partners, the use of different catalyst systems, by employing modified reaction conditions, or utilizing different substrates to obtain the desired target molecules. The details of the syntheses and the evolution of the synthetic strategies will be described in this presentation. |
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Physical Organic, Materials, Heterocycles, Aromatics, Metal-Mediated Reactions
8:00 PM-10:00 PM, Tuesday, September 9, 2003 Hilton New York -- Americas Hall 1, Poster
Division of Organic Chemistry |