By Brian P. Johnson, Gabor Balazs, Manfred Scheer (auth.), Jean-Pierre Majoral (eds.)
B.P Johnson, G. Balazs, M. Scheer: Complexes with a Metal-Phosphorus Triple Bond.- M. Tanaka: Homogeneous Catalysis for H-P Bond Addition Reactions.- J.P. Dutasta: New Phosphorylated Hosts for the layout of recent Supramolecular Assemblies.- J. Michalski, W. Dabkowski: state-of-the-art. Chemical Synthesis of Biophosphates and Their Analogues through PIII Derivatives.- A. Vioux, J. Le Bideau, P.H. Mutin, D. Leclercq: Hybrid Organic-Inorganic fabrics in keeping with Organophosphorus Derivatives.- D. Gudat: Zwitterionic Phospholide Derivatives-New Ambiphilic Ligands.- Y. Takagi, Y. Ikeda, ok. Taira: Ribozyme Mechanisms.
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26 2 Metal Complex-Catalyzed Addition of the P(III)-H Bond to Unsaturated Compounds . . . . . . . . . . . . . 4 Transition Metal-Catalyzed Addition of PH3 to Formaldehyde . Transition Metal-Catalyzed Addition of PH3 to Alkenes . . . Transition Metal-Catalyzed Addition of the P(III)-H Bond to Alkynes . . . . . . . . . . . . . . . . . Lanthanide Metal-Catalyzed Addition. . . . . . . . . .. 31 33 3 Transition Metal-Catalyzed Addition of Hydrogen Phosphonate .
2 Addition to Alkenes and Dienes Alkenes are much less reactive in the H-P bond addition reactions than alkynes. However, 1,3,2-dioxaphospholane 2-oxide (4a), a five-membered hydrogen phosphonate of pinacol, is exceptionally reactive with alkenes although dialkyl and diaryl phosphonates such as 4b–d are totally unreactive (Scheme 25) . Very interestingly, six-membered hydrogen phosphonates 4e,f are also unreactive under identical conditions. Scheme 25 As Scheme 26 demonstrates, the terminal alkene reactions using palladium-dppb [dppb=1,4-bis(diphenylphosphino)butane] catalyst systems usual- Scheme 26 42 Masato Tanaka ly form linear phosphonates with high regioselectivities.
Reductive elimination from complex 13a proceeded readily affording methylphosphonate 14a while 13b was totally unreactive. On the basis of these results, it can be safely concluded that the rate-determining step is the reductive elimination process, which is the provenance of the significant reactivity difference depending on the structure of the alcohol moiety. Stockland and coworkers also studied the C-P(O) reductive elimination from (bipy)PdMe[P(O)(OPh)2] and related complexes to reconfirm the lack of the reactivity.