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1,3-Bis(diphenylphosphino)propane

1,3-Bis(diphenylphosphino)propane (dppp) is an organophosphorus compound with the formula PhP(CH)PPh. The compound is a white solid that is soluble in organic solvents. It is slightly air-sensitive, degrading in air to the phosphine oxide. It is classified as a diphosphine ligand in coordination chemistry and homogeneous catalysis.

The diphosphine can be prepared by the reaction of lithium diphenylphosphide and 1,3-dichloropropane (Ph = CH): : 2 PhPLi + Cl(CH)Cl → PhP(CH)PPh + 2 LiCl

However, it can be synthesised via a much more controllable (and cheaper) route, via metal-halogen exchange and then metathesis: :Br(CH)Br + 2 BuLi → Li(CH)Li + 2 BuBr :Li(CH)Li + 2 PCl → ClP(CH)PCl + 2 LiCl :ClP(CH)PCl + 4 PhLi → PhP(CH)PPh + 4 LiCl

Coordination chemistry and use as co-catalyst

The diphosphine serves as a bidentate ligand forming six-membered CPM chelate ring with a natural bite angle of 91°. For example, the complex dichloro(1,3-bis(diphenylphosphino)propane)nickel is prepared by combining equimolar portions of the ligand and nickel(II) chloride hexahydrate. This nickel complex serves as a catalyst for the Kumada coupling reaction. Dppp is also used as a ligand for palladium(II) catalysts to co-polymerize carbon monoxide and ethylene to give polyketones. Dppp can sometimes be used in palladium-catalyzed arylation under Heck reaction conditions to control regioselectivity.

References

References

  1. (2009). "Bite angle effects of diphosphines in C–C and C–X bond forming cross coupling reactions". Chemical Society Reviews.
  2. Kumada, Makota. (1988). "Phosphine-Nickel Complex Catalyzed Cross-Coupling of Grignard Reagents with Aryl and Alkenyl Halides: 1,2-dibutylbenzene".
  3. (2001). "Polyketones".
  4. 10.1021/jo00031a029
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