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• W2004273116 abstract "A highly enantioselective intermolecular hydrophosphination reaction is described. The (Pigiphos)nickel(II)-catalyzed reaction of secondary phosphines and methacrylonitrile gives chiral 2-cyanopropylphosphines in good yield and high enantiomeric excess (ee's up to 94%; (R)-(S)-Pigiphos = bis{(R)-1-[(S)-2-(diphenylphosphino)ferrocenyl]ethyl}cyclohexylphos phine). We propose a mechanism involving coordination of methacrylonitrile to the dicationic nickel catalyst followed by 1,4-addition of the phosphine, and then, rate-determining proton transfer. This mechanism is supported by (a) the experimentally determined rate law (rate = k‘[Ni][methacrylonitrile][t-Bu2PH]), (b) a large primary deuterium isotope effect kH/kD = 4.6(1) for the addition of t-Bu2PH(D) at 28.3 °C in toluene-d8, (c) the isolation and characterization of the species [Ni(κ3-Pigiphos)(κN-methacrylonitrile)]2+, and (d) DFT calculations of model compounds." @default.
• W2004273116 created "2016-06-24" @default.
• W2004273116 creator A5015422195 @default.
• W2004273116 creator A5039255382 @default.
• W2004273116 date "2005-11-10" @default.
• W2004273116 modified "2023-10-16" @default.
• W2004273116 title "Enantioselective Addition of Secondary Phosphines to Methacrylonitrile: Catalysis and Mechanism" @default.
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• W2004273116 doi "https://doi.org/10.1021/ja0555163" @default.
• W2004273116 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/16316248" @default.
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