ORGN 163 |
| We introduce Cp*CH2PPh2 (1, Cp*=1,2,3,4,5–pentamethyl–2,4–cyclopentadienyl), a monophosphine ligand with a pendant 1,3–diene moiety. We envisioned that the 1,3–diene part as well as the phosphorous atom would coordinate to transition metal and that 1 would thus serve as a new six–electron donating ligand. Cross–coupling reactions of alkyl halides are rather difficult reactions, compared to those of aryl or alkenyl halides, since intermediary alkylmetal complexes are prone to undergo β–hydride elimination. We expected that the diene moiety of 1 would advantageously occupy vacant coordination sites necessary for the β–hydride elimination. We chose nickel–catalyzed cross–coupling reaction of primary alkyl bromides with phenylmagnesium bromide. The reaction was successful, quantitatively yielding corresponding phenylated products.
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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 |
