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

[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)PdCl{{sub|2}}]. This commercially available material can be prepared by reacting dppf with a suitable nitrile complex of palladium dichloride:^[1]

dppf + PdCl(RCN) → (dppf)PdCl + 2 RCN (RCN = CHCN or CHCN)

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]

Notes and References

1. Nataro . Chip . Fosbenner . Stephanie M. . Synthesis and Characterization of Transition-Metal Complexes Containing 1,1'-Bis(diphenylphosphino)ferrocene . . 86 . 1412–1415 . 2009 . 12 . 10.1021/ed086p1412. 2009JChEd..86.1412N.
2. Reactions of the 21st Century: Two Decades of Innovative Catalyst Design for Palladium-Catalyzed Cross-Couplings. Peter G.. Gildner. Thomas J.. Colacot. Organometallics. 2015. 34. 23. 5497–5508. 10.1021/acs.organomet.5b00567.
3. Book: Modern Organic Synthesis in the Laboratory: A Collection of Standard Experimental Procedures. Jie Jack. Li. Chris. Limberakis. Derek A.. Pflum. Oxford University Press. 2007. 9780198040637. 111–. Carbon - Carbon Bond Formation. https://books.google.com/books?id=kTQNYINDXpkC&q=Pd(dppf)Cl2&pg=PA3.
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. 10.1021/ja9608306.
5. Palladium-Catalyzed Reductive Homocoupling of Aromatic Halides and Oxidation of Alcohols. Minfeng. Zeng. Yijun. Du. Linjun. Shao. Chenze. Qi. Xian-Man. Zhang. J. Org. Chem.. 2010. 75. 8. 2556–2563. 10.1021/jo100089d. 20302294.