1,3-Bis(diphenylphosphino)propane
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| Abbreviations | DPPP |
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1,3-Bis(diphenylphosphino)propane (dppp) is an organophosphorus compound with the formula Ph2P(CH2)3PPh2. 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 = C6H5):
- 2 Ph2PLi + Cl(CH2)3Cl → Ph2P(CH2)3PPh2 + 2 LiCl
However, it can be synthesised via a much more controllable (and cheaper) route, via metal-halogen exchange and then metathesis:
- Br(CH2)3Br + 2 tBuLi → Li(CH2)3Li + 2 tBuBr
- Li(CH2)3Li + 2 PCl3 → Cl2P(CH2)3PCl2 + 2 LiCl
- Cl2P(CH2)3PCl2 + 4 PhLi → Ph2P(CH2)3PPh2 + 4 LiCl
Coordination chemistry and use as co-catalyst
The diphosphine serves as a bidentate ligand forming six-membered C3P2M chelate ring with a natural bite angle of 91°.[1] 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.[2] Dppp is also used as a ligand for palladium(II) catalysts to co-polymerize carbon monoxide and ethylene to give polyketones.[3] Dppp can sometimes be used in palladium-catalyzed arylation under Heck reaction conditions to control regioselectivity.[4]
References
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- ↑ Cabri, Walter; Candiani, Ilaria; Bedeschi Angelo; Penco, Sergio"α-Regioselectivity in Palladium-Catalyzed Arylation of Acyclic Enol Ethers" journal= Journal of Organic Chemistry, 1991, volume 57, p. 1481. Script error: No such module "CS1 identifiers".
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