ORGN 112 |
| A fast one-pot method has been developed for the direct preparation of 3-aryl-1,2-cyclohexandiones (2) from 2,3-epoxycyclohexanone (1) via a microwave-assisted tandem isomerization-Heck arylation reaction. Within 20-30 minutes of directed microwave heating 58-72% yield of 2 were isolated. The protocol is over all environmentally benign – employing less than 0.05 mol-% palladium acetate and no phosphine ligand. The preparative reactions were performed in 50% aqueous polyethyleneglycol utilizing sodium acetate as a base. The acetate base, but not the palladium, was found to promote the isomerization of 1 into 1,2-cyclohexandion (3). A classical procedure for isomerization-arylation of 1 in DMF is also reported.
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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 |
