ORGN 147 |
| The novel palladium-catalyzed reaction of aryl halides with functionalized, CH-acidic methanesulfonamides has been developed for the preparation of benzylic sulfonamides, useful building blocks for organic synthesis. Appropriate conditions were developed by judicious choice of ligand and base, allowing the coupling of numerous aryl halides with ester- or amide-substituted sulfonamides. Electron-poor, electron-rich, and hindered aryl bromides, as well as heteroaryl halides, were tolerated in the cross-coupling, yielding moderate to excellent yields of the monoarylated sulfonamides. Importantly, in-situ quenching of the cross-coupling products with various electrophiles (e.g. MeI, N-chlorosuccinimide) afforded products containing functionalized quaternary carbon centers in a two-step, one-pot process. Further derivatization of the products was also accomplished through an amine-promoted sulfonamide metathesis/decarboxylation reaction.
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Process R&D, Physical Organic Chemistry, Heterocycles, Aromatics, Metal-Mediated Reactions
8:00 PM-10:00 PM, Sunday, March 25, 2007 Hyatt Regency Chicago -- Riverside Center, Poster
Division of Organic Chemistry |
