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

[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)
[1,1'-Bis(diphenylphosphino)ferrocene]­palladium(II) dichloride
Names
IUPAC name
[1,1'-Bis(diphenylphosphino)ferrocene-κ2P,P']dichloropalladium(II)
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.106.747
EC Number
  • 615-748-9
  • InChI=1S/2C17H14P.2ClH.Fe.Pd/c2*1-3-9-15(10-4-1)18(17-13-7-8-14-17)16-11-5-2-6-12-16;;;;/h2*1-14H;2*1H;;/q;;;;;+2/p-2 checkY
    Key: JCWIWBWXCVGEAN-UHFFFAOYSA-L checkY
  • [CH-]1C=CC=C1P(C2=CC=CC=C2)C3=CC=CC=C3.[CH-]1C=CC=C1P(C2=CC=CC=C2)C3=CC=CC=C3.Cl[Pd]Cl.[Fe+2]
Properties
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

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
  1. Nataro, Chip; Fosbenner, Stephanie M. (2009). "Synthesis and Characterization of Transition-Metal Complexes Containing 1,1'-Bis(diphenylphosphino)ferrocene". J. Chem. Educ. 86 (12): 1412–1415. Bibcode:2009JChEd..86.1412N. 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. John P. Wolfe; Seble Wagaw; Stephen L. Buchwald (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. PMID 20302294.
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