ORGN 559 |
| Nature relies on the use of thiophilic metals such as Ni to achieve the selective activation of soft, polarizable C-S substrates in a hard, aqueous environment. Using sulfur based leaving groups to construct C-C bonds, our lab has published a series of bio-inspired cross-coupling reactions of organosulfur compounds with boronic acids mediated by palladium and an activating copper cofactor [Cu(I)-OC(O)R]. These conditions have been used to synthesize ketones, alkynes, amidines, heteroaromatics, and functionalized pyrimidones. However, these reactions produce a catalytically inactive Cu(I)-SR, and, therefore, require a stoichiometric copper source. Biological principles were exploited to answer the fundamental question: Can we activate Cu(I)-SR and scavenge sulfur under mild oxidative conditions to render a completely catalytic ketone synthesis?
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Heterocycles, Aromatics, Metal-Mediated Reactions and Syntheses, Materials, Devices, and Switches
8:00 PM-10:00 PM, Wednesday, 29 March 2006 Georgia World Congress Center -- Ex. Hall B4, Poster
Sci-Mix
Division of Organic Chemistry |
