1,3-Bis(diphenylphosphino)propane

1,3-Bis(diphenylphosphino)propane

Names
IUPAC name Propane-1,3-diylbis(diphenylphosphane)
Identifiers
CAS Number	6737-42-4 Y
Abbreviations	DPPP
ChEMBL	ChEMBL73394 Y
ChemSpider	73276 Y
Jmol interactive 3D	Image Image
PubChem	81219
InChI InChI=1S/C27H26P2/c1-5-14-24(15-6-1)28(25-16-7-2-8-17-25)22-13-23-29(26-18-9-3-10-19-26)27-20-11-4-12-21-27/h1-12,14-21H,13,22-23H2 Y Key: LVEYOSJUKRVCCF-UHFFFAOYSA-N Y InChI=1/C27H26P2/c1-5-14-24(15-6-1)28(25-16-7-2-8-17-25)22-13-23-29(26-18-9-3-10-19-26)27-20-11-4-12-21-27/h1-12,14-21H,13,22-23H2 Key: LVEYOSJUKRVCCF-UHFFFAOYAP
SMILES P(c1ccccc1)(c2ccccc2)CCCP(c3ccccc3)c4ccccc4 c1ccc(cc1)P(CCCP(c2ccccc2)c3ccccc3)c4ccccc4
Properties
Chemical formula	C27H26P2
Molar mass	412.45 g·mol−1
Appearance	white solid
Solubility in water	chlorocarbons
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

1,3-Bis(diphenylphosphino)propane (dppp) is an organophosphorus compound with the formula (CH₂)₃(P(C₆H₅)₂)₂. 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 + C₃H₆Cl₂ → C₃H₆(PPh₂)₂ + 2 LiCl

Coordination chemistry and use as co-catalyst

The diphosphine serves as a bidentate ligand forming six-membered C₃P₂M chelate ring. 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.^[1] Dppp is also used as a ligand for palladium(II) catalysts to co-polymerize carbon monoxide and ethylene to give polyketones.^[2] Dppp can sometimes be used in palladium-catalyzed arylation under Heck reaction conditions to control regioselectivity.^[3]

References

1. ↑ Kumada, Makota; Tamao, Kohei; Sumitani, Koji (1988). "Phosphine-Nickel Complex Catalyzed Cross-Coupling of Grignard Reagents with Aryl and Alkenyl Halides: 1,2-dibutylbenzene". Org. Synth. ; Coll. Vol. 6, p. 407 
2. ↑ Drent, E.; Mul, W. P.; Smaardijk, A. A. (2001). "Polyketones". Encyclopedia Of Polymer Science and Technology. doi:10.1002/0471440264.pst273. 
3. ↑ 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. doi:10.1021/jo00031a029