(1,1'-Bis(diphenylphosphino)ferrocene)palladium(II) dichloride

[1,1'-Bis(diphenylphosphino)ferrocene]palladium(II) dichloride
Identifiers
CAS Number	72287-26-4 ; 95464-05-4 complex with DCM ;
ChemSpider	24602493 ;
ECHA InfoCard	100.106.747
	InChI InChI=1S/2C17H14P.2ClH.Fe.Pd/c21-3-9-15(10-4-1)18(17-13-7-8-14-17)16-11-5-2-6-12-16;;;;/h21-14H;2*1H;;/q;;;;;+2/p-2 Key: JCWIWBWXCVGEAN-UHFFFAOYSA-L ;
Properties
Chemical formula	C34H28Cl2FeP2Pd
Molar mass	731.71 g·mol−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

[1,1'‑Bis(diphenylphosphino)ferrocene]palladium(II) dichloride is a palladium complex containing the bidentate ligand 1,1'-bis(diphenylphosphino)ferrocene (dppf), abbreviated as [(dppf)PdCl₂]. This commercially available material can be prepared by reacting dppf with a suitable nitrile complex of palladium dichloride:[1]

dppf + PdCl₂(RCN)₂ → (dppf)PdCl₂ + 2 RCN (RCN = CH₃CN or C₆H₅CN)

The compound is popularly used for palladium-catalyzed coupling reactions,[2][3] such as the Buchwald–Hartwig amination[4] and the reductive homocoupling of aryl halides.[5]

Examples of Buchwald-Hartwig aminations using second generation catalysts including [(dppf)PdCl₂]

References

Nataro, Chip; Fosbenner, Stephanie M. (2009). "Synthesis and Characterization of Transition-Metal Complexes Containing 1,1'-Bis(diphenylphosphino)ferrocene". J. Chem. Educ. 86: 1412–1415. doi:10.1021/ed086p1412.
Gildner, Peter G.; Colacot, Thomas J. (2015). "Reactions of the 21st Century: Two Decades of Innovative Catalyst Design for Palladium-Catalyzed Cross-Couplings". Organometallics. 34 (23): 5497–5508. doi:10.1021/acs.organomet.5b00567.
Li, Jie Jack; Limberakis, Chris; Pflum, Derek A. (2007). "Carbon–Carbon Bond Formation". Modern Organic Synthesis in the Laboratory: A Collection of Standard Experimental Procedures. Oxford University Press. pp. 111-. ISBN 9780198040637.
Wolfe, John P.; Wagaw, Seble; Buchwald, Stephen L. (1996). "An Improved Catalyst System for Aromatic Carbon-Nitrogen Bond Formation: The Possible Involvement of Bis(Phosphine) Palladium Complexes as Key Intermediates". J. Am. Chem. Soc. 118 (30): 7215–7216. doi:10.1021/ja9608306.
Zeng, Minfeng; Du, Yijun; Shao, Linjun; Qi, Chenze; Zhang, Xian-Man (2010). "Palladium-Catalyzed Reductive Homocoupling of Aromatic Halides and Oxidation of Alcohols". J. Org. Chem. 75 (8): 2556–2563. doi:10.1021/jo100089d.

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[nataro-1] Nataro, Chip; Fosbenner, Stephanie M. (2009). "Synthesis and Characterization of Transition-Metal Complexes Containing 1,1'-Bis(diphenylphosphino)ferrocene". J. Chem. Educ. 86: 1412–1415. doi:10.1021/ed086p1412.

[2] Gildner, Peter G.; Colacot, Thomas J. (2015). "Reactions of the 21st Century: Two Decades of Innovative Catalyst Design for Palladium-Catalyzed Cross-Couplings". Organometallics. 34 (23): 5497–5508. doi:10.1021/acs.organomet.5b00567.

[3] Li, Jie Jack; Limberakis, Chris; Pflum, Derek A. (2007). "Carbon–Carbon Bond Formation". Modern Organic Synthesis in the Laboratory: A Collection of Standard Experimental Procedures. Oxford University Press. pp. 111-. ISBN 9780198040637.

[4] Wolfe, John P.; Wagaw, Seble; Buchwald, Stephen L. (1996). "An Improved Catalyst System for Aromatic Carbon-Nitrogen Bond Formation: The Possible Involvement of Bis(Phosphine) Palladium Complexes as Key Intermediates". J. Am. Chem. Soc. 118 (30): 7215–7216. doi:10.1021/ja9608306.

[5] Zeng, Minfeng; Du, Yijun; Shao, Linjun; Qi, Chenze; Zhang, Xian-Man (2010). "Palladium-Catalyzed Reductive Homocoupling of Aromatic Halides and Oxidation of Alcohols". J. Org. Chem. 75 (8): 2556–2563. doi:10.1021/jo100089d.