page_title: Hydrophosphination
section_title: Late transition metal catalysts
hierarchical_section_title: Hydrophosphination / Metal-catalyzed reactions / Late transition metal catalysts
caption_attribution_description: English: used for hydrophosphination
context_page_description: Hydrophosphination is the insertion of a carbon-carbon multiple bond into a phosphorus-hydrogen bond forming a new phosphorus-carbon bond. Like other hydrofunctionalizations, the rate and regiochemistry of the insertion reaction is influenced by the catalyst. Catalysts take many forms, but most prevalent are bases and free-radical initiators.
context_section_description: Late transition metal hydrophosphination catalysts, i.e. those reliant on the nickel-triad and neighboring elements, generally require alkenes and alkynes with electron withdrawing substituents.  A strong base is required as a cocatalyst. 
  Some late metal hydrophosphination catalysts proceed via oxidative addition of a P-H bond. For example, a Pt(0) catalyst undergoes oxidative addition of a secondary phosphine to form the corresponding hydrido Pt(II) phosphido complex. These systems catalyze hydrophosphination of acrylonitrile, although this reaction can be achieved without metal catalysts.  The key P-C bond-forming step occurs through an outer-sphere, Michael-type addition.
  The usual mechanism for hydrophosphination for late metal catalysts involves insertion of the alkene into the metal-phosphorus bond. Insertion into the metal-hydrogen bond is also possible. The product phosphine is produced through reductive elimination of a P-C bond rather than a P-H bond in Glueck's system. The Ni(0) catalyst involves oxidation addition of a P-H bond to the metal, followed by insertion of the alkene into the M-H bond.
caption: Mechanism proposed for hydrophosphination catalyzed by a Pt(II) phosphido complex.
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