Synthesis of allylamides from allyl halides, carbon monoxide, and titanium-nitrogen complexes prepared from molecular nitrogen |
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Authors: | Kazutaka Ueda |
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Institution: | Graduate School of Pharmaceutical Sciences, Hokkaido University, Sapporo 060-0812, Japan |
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Abstract: | 4-Phenylbut-3-enamide could be synthesized from corresponding 3-chloroprop-2-enylbenzene, carbon monoxide (1 atm), and titanium-nitrogen complexes, prepared from Ti(OiPr)4, Li, TMSCl, and molecular nitrogen (1 atm), using a palladium catalyst. The reaction proceeds via transmetalation of the titanium-nitrogen complex to an acylpalladium complex. PtBu3 as a ligand of the palladium catalyst, afforded a good result, and the amounts of Li and TMSCl affected the yield of amide. When the reaction was carried out using a bidentate ligand on the palladium complex under an atmosphere of argon instead of carbon monoxide, an allylamine derivative was obtained. |
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