ORGN 194 |
There is currently extensive interest in chemoselective hydrogenation methods using catalytic poisons. While many catalyst poisons have been evaluated to obtain chemoselective catalytic systems, only a few studies, such as the Lindlar catalyst and Rosenmund's reaction, have been accepted as applicable methodologies. Recently, we found that the addition of diphenylsulfide dramatically suppressed the catalyst activity of Pd/C toward many reducible functionalities such as aromatic ketone, aromatic aldhyde, aryl chloride, N-Cbz and benzyl ester except for olefin, acetylene and azide functionalities. In this presentation, we presene the development of a heterogeneous Pd/C-diphenylsulfide complex catalyst (Pd/C[Ph2S]) that processes quite low catalyst activity by the coordinating of diphenylsulfide acts as a mild catalyst poison. Pd/C[Ph2S] selectively catalyzed the hydrogenation of multiple bonds, azide, aromatic nitro and aromatic aldehyde functionalities without the reduction of many other reducible functionalities.
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Asymmetric Reactions and Syntheses, Metal-Mediated Reactions, Combinatorial, Parallel, and Solid-Phase Chemistry
8:00 PM-10:00 PM, Sunday, 10 September 2006 Moscone Center -- Hall D, Poster
Division of Organic Chemistry |
