ORGN 359 |
| Karl S. A. Vallin1, Qisheng Zhang2, Mats Larhed1, Dennis P. Curran2, and Anders Hallberg3. (1) Department of Organic Pharmaceutical Chemistry, Uppsala University, BMC, Box-574, SE-751 23 Uppsala, Sweden, (2) Department of Chemistry, University of Pittsburgh, 219 Parkman Ave., Pittsburgh, PA 15260, (3) Department of Organic Pharmaceutical Chemistry, BMC, Uppsala University, Box 596, S-75124 Uppsala, Sweden |
| We have performed internal ligand-controlled Heck vinylations of enamides with high regioselectivity in moderate to good yields. New bidentate fluorous-tagged 1,3-bis(diphenylphosphino) propane ligands (F-dppp’s) were synthesized and examined. The cationic vinylations of the enamides with F-dppp ligands rendered essentially the same internal selectivity and catalytic activity as in those vinylations where non-fluorous ligands were employed. After reaction, the fluorous-tagged ligand material was easily removed by convenient solid fluorous phase separation. In addition, controlled microwave heating accelerated the palladium-catalyzed reactions and full conversions were achieved after reaction times of only 15-30 min. |
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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 |