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(1,1'-Bis(diphenylphosphino)ferrocene)palladium(II) dichloride
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Chemical compound
[1,1'-Bis(diphenylphosphino)ferrocene]palladium(II) dichloride bracket substitution
{{Chembox
| Name = [1,1'-Bis(diphenylphosphino)ferrocene]palladium(II) dichloride
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| verifiedrevid = 477200316
| ImageFile = Bis(diphenylphosphino)ferrocene palladium(II) dichloride.svg
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| ImageFile1 = Dppf-PtCl2-from-xtal-3D-balls-B.png
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| ImageSize = 150px
| IUPACName = Dichlorido[(ferrocene-1,1′-diyl)bis(diphenylphosphane-κP)]palladium
| OtherNames = [1,1'-Bis(diphenylphosphino)ferrocene-κ2P,''P]dichloropalladium(II)
| Section1 = 72287-26-4 changed 95464-05-4 complex with DCM correct correct FDA SZ5WB9HNQ6 correct chemspider 24602493 615-748-9 71310626 [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] correct chemspider 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 correct chemspider JCWIWBWXCVGEAN-UHFFFAOYSA-L
| Section2 = 34 28 2 1 2 1
}}[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: Nataro Chip Fosbenner Stephanie M. Synthesis and Characterization of Transition-Metal Complexes Containing 1,1'-Bis(diphenylphosphino)ferrocene J. Chem. Educ. 86 1412–1415 2009 12 10.1021/ed086p1412 2009JChEd..86.1412N
dppf + PdCl2(RCN)2 → (dppf)PdCl2 + 2 RCN (RCN = CH3CN or C6H5CN)
A mechanochemical approach for the synthesis of this compound has also recently been reported. The method involves the direct use of PdCl2 with the exact amount of dppf, obtaining the final complex in 60 minutes.RSC Mechanochemistry 2026 3 115–130 Rapid, efficient and green solid-state mechanosynthesis of palladium complexes L. Genesin E. Aneggi W. Baratta T. Munir F. Trigatti D. Zuccaccia 1 10.1039/D5MR00107B free 11390/1321444 free
The compound is popularly used for palladium-catalyzed coupling reactions, 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 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 such as the Buchwald–Hartwig aminationJohn 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 and the reductive homocoupling of aryl halides. 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
thumb|class=skin-invert-image|center|600px|Examples of Buchwald-Hartwig aminations using second generation catalysts including [(dppf)PdCl2]
References
Category:Palladium compounds
Category:Phosphine complexes
Category:Catalysts
Category:Ferrocenes
Category:Chloro complexes