ORGN 216 |
| Metal-catalyzed nitrene transfer reactions are an attractive route to produce biologically and synthetically important molecules such as amines and aziridines. Although much progress has been made in nitrene transfer reactions utilizing [N-(p-toluenesulfonyl) imino]phenyliodinane (PhI=NTs), the nitrene source suffers from several drawbacks. Consequently, there has been growing interest in developing catalytic nitrene transfer reactions using alternate nitrene sources. Previously, we have reported the use of alternate nitrene sources, such as bromamine-T and diphenylphosphorylazide, for nitrene transfer reactions catalyzed by metalloporphyrins. In our continuing studies to develop metalloporphyrin-catalyzed nitrene transfer reactions, we will report that arylsulfonyl azides are a class of suitable nitrene sources utilizing cobalt complexes of porphyrins as catalysts. The cobalt-catalyzed process can proceed under mild and neutral conditions in low catalyst loading without the need of other additives, while generating nitrogen gas as the only byproduct. These processes produce synthetically and biologically valuable nitrogen-containing compounds. |
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Metal-Mediated Reactions and Synthesis
8:00 AM-12:00 PM, Monday, April 7, 2008 Morial Convention Center -- Rm. R06, Oral
Division of Organic Chemistry |