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 ;
3D model (JSmol)	Interactive image;
ChemSpider	21241481 ;
ECHA InfoCard	100.132.628
	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	External SDS
GHS pictograms	[1]
GHS signal word	Danger[1]
GHS hazard statements	H315, H317, H319, H334, H335, H350[1]
GHS precautionary statements	P201, P261, P280, P305+351+338, P308+313[1]
	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.^[2]

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

Reactions

NiCl₂(dppp) in an effective catalyst for coupling reactions such as the Kumada coupling^[2] and Suzuki reactions (example below).^[3] It also catalyzes other reactions that convert enol ethers, dithioacetals, and vinyl sulfides to olefins.^[4]^[5]

References

1 2 3 4 "1,3-Bis(diphenylphosphino)propane Nickel(II) Chloride". American Elements. Retrieved September 6, 2018.
1 2 Kumada, Makota; Tamao, Kohei; Sumitani, Koji (1988). "Phosphine-Nickel Complex Catalyzed Cross-Coupling of Grignard Reagents with Aryl and Alkenyl Halides: 1,2-dibutylbenzene". Organic Syntheses. ; Collective Volume, 6, p. 407
↑ 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.
↑ Tien-Yau Luh; Tien-Min Yuan. "Cross-Coupling Reactions". Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rd100.pub2.
↑ 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.

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[sds-1] 1 2 3 4 "1,3-Bis(diphenylphosphino)propane Nickel(II) Chloride". American Elements. Retrieved September 6, 2018.

[kumada-2] 1 2 Kumada, Makota; Tamao, Kohei; Sumitani, Koji (1988). "Phosphine-Nickel Complex Catalyzed Cross-Coupling of Grignard Reagents with Aryl and Alkenyl Halides: 1,2-dibutylbenzene". Organic Syntheses. ; Collective Volume, 6, p. 407

[3] 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.

[4] Tien-Yau Luh; Tien-Min Yuan. "Cross-Coupling Reactions". Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rd100.pub2.

[5] 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.