Dichloro[1,3-bis(diphenylphosphino)propane]nickel

Dichloro(1,3-bis(diphenylphosphino)propane)nickel

Names
Systematic IUPAC name Dichloro[1,3-propanediylbis(diphenylphosphanuide-kappaP)]nickel
Other names 1,3-bis(diphenylphosphino)propanenickel(II) chloride
Identifiers
CAS Number	15629-92-2
ChemSpider	21241481
Jmol interactive 3D	Image
InChI InChI=1S/C27H26P2.2ClH.Ni/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;2*1H;
SMILES Cl[Ni]3(Cl)P(CCCP3(c1ccccc1)c2ccccc2)(c4ccccc4)c5ccccc5
Properties
Chemical formula	C27H26Cl2NiP2
Molar mass	542.05 g·mol^−1
Appearance	Orange to red-orange powder
Melting point	213 °C (415 °F; 486 K)
Solubility in water	immiscible in water
Hazards
Safety data sheet
R-phrases	R49 R36/37/38 R42/43
S-phrases	S53 R26 S36/37/39 S45
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

Dichloro[1,3-bis(diphenylphosphino)propane]nickel a coordination complex with the formula NiCl₂(dppp); where dppp is the diphosphine 1,3-bis(diphenylphosphino)propane. It is used as a catalyst in organic synthesis. The compound is a bright orange-red crystalline powder.

Structure and properties

The compound has idealized C_2v symmetry, ignoring orientation of the phenyl groups. The Nickel has square planar geometry. The compound is soluble in non-polar organic solvents and is diamagnetic.

Preparation

NiCl₂(dppp) is prepared by combining equal molar portions of nickel(II) chloride hexahydrate with 1,3-bis(diphenylphosphino)propane in 2-propanol.^[1]

Ni(H₂O)₆Cl₂ + dppp → NiCl₂(dppp) + 6 H₂O

Reactions

NiCl₂(dppp) in an effective catalyst for coupling reactions such as the Kumada coupling^[1] and Suzuki reactions (example below).^[2] It also catalyzes other reactions that convert enol ethers, dithioacetals, and vinyl sulfides to olefins.^[3][4]

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. Zhao, Yu-Long; Li, You; Li, Shui-Ming; Zhou, Yi-Guo; Sun, Feng-Yi; Gao, Lian-Xun; Han, Fu-She (1 June 2011). "A Highly Practical and Reliable Nickel Catalyst for Suzuki-Miyaura Coupling of Aryl Halides". Advanced Synthesis & Catalysis 353 (9): 1543–1550. doi:10.1002/adsc.201100101.
3. Tien-Yau Luh; Tien-Min Yuan. "Cross-Coupling Reactions". Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rd100.pub2.
4. Ljungdahl, Thomas; Bennur, Timmanna; Dallas, Andrea; Emtenaes, Hans; Maartensson, Jerker (2008). "Two Competing Mechanisms for the Copper-Free Sonogashira Cross-Coupling Reaction". Organometallics 27 (11): 2490–2498. doi:10.1021/om800251s.