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

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[1,1'-Bis(diphenylphosphino)ferrocene]palladium(II) dichloride
Bis(diphenylphosphino)ferrocene palladium(II) dichloride.svg
Identifiers
ChemSpider
ECHA InfoCard 100.106.747
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

[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[edit]

  1. ^ Nataro, Chip; Fosbenner, Stephanie M. (2009). "Synthesis and Characterization of Transition-Metal Complexes Containing 1,1'-Bis(diphenylphosphino)ferrocene". J. Chem. Ed. 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.