| Revision as of 15:48, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 467590474 of page 1,1'-Bis(diphenylphosphino)ferrocene for the Chem/Drugbox validation project (updated: 'CASNo'). |
Latest revision as of 13:52, 11 January 2024 edit RMCD bot (talk | contribs)Bots, Template editors999,681 edits Removing notice of move discussionTag: Manual revert |
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}} |
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{{chembox |
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{{chembox |
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| Name=1,1{{prime}}-Bis(diphenylphosphino){{SHY}}ferrocene |
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| verifiedrevid = 401202503 |
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|Verifiedfields = correct |
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| ImageFile = Dppf.png |
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|Watchedfields = changed |
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| ImageSize = 150 px |
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|verifiedrevid = 477199791 |
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| ImageFile1 = Dppf-from-xtal-3D-balls.png |
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|ImageFile = Dppfnew.png |
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| ImageSize1 = 250 px |
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|ImageSize = 150px |
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| IUPACName = 1,1'- bis( diphenylphosphanyl) ferrocene |
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|ImageFile1 = Dppf-from-xtal-3D-balls.png |
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| OtherNames = 1,1'- Bis( diphenylphosphino) ferrocene, 1,1'- Ferrocenediyl- bis(diphenylphosphine), Dppf, 1,1'- Ferrocenebis (diphenylphosphine) |
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|ImageSize1 = 250px |
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| Section1 = {{Chembox Identifiers |
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|PIN = (Ferrocene-1,1{{prime}}-diyl)bis(diphenylphosphane) |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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|OtherNames = 1,1{{prime}}-Bis(diphenylphosphino)ferrocene, 1,1{{prime}}-ferrocenediylbis(diphenylphosphine), Dppf, 1,1{{prime}}-ferrocenebis(diphenylphosphine), 1,1{{prime}}-bis(diphenylphosphanyl)ferrocene |
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| ChEBI = 30743 |
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|Section1={{Chembox Identifiers |
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| ChemSpiderID = 21865114 |
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|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| InChI = 1/2C17H14P.Fe/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;/q2*-1;+2 |
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|ChEBI_Ref = {{ebicite|correct|EBI}} |
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| InChIKey = HPXNTHKXCYMIJL-UHFFFAOYSA-N |
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|ChEBI = 30743 |
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| InChI1 = 1/2C17H14P.Fe/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;/rC34H28FeP2/c1-5-13-21(14-6-1)36(22-15-7-2-8-16-22)33-29-25-26-30(33)35(25,26,29,33)27-28(35)32(35)34(35,31(27)35)37(23-17-9-3-10-18-23)24-19-11-4-12-20-24/h1-20,25-32H |
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|ChemSpiderID = 21865114 |
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| InChIKey1 = HPXNTHKXCYMIJL-KDKHWAOJAX |
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|EINECS = 640-119-0 |
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| SMILES1 = c1ccc(cc1)P(c2ccccc2)C34C53678912(C5C6C74)C3C8C9C1(C23)P(c1ccccc1)c1ccccc1 |
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|Gmelin = 24075 |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 1S/2C17H14P.Fe/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; |
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|InChI = 1/2C17H14P.Fe/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;/q2*-1;+2 |
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|InChIKey = HPXNTHKXCYMIJL-UHFFFAOYSA-N |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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|InChI1 = 1/2C17H14P.Fe/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;/rC34H28FeP2/c1-5-13-21(14-6-1)36(22-15-7-2-8-16-22)33-29-25-26-30(33)35(25,26,29,33)27-28(35)32(35)34(35,31(27)35)37(23-17-9-3-10-18-23)24-19-11-4-12-20-24/h1-20,25-32H |
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| StdInChIKey = HPXNTHKXCYMIJL-UHFFFAOYSA-N |
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|InChIKey1 = HPXNTHKXCYMIJL-KDKHWAOJAX |
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| CASNo = <!-- blanked - oldvalue: 12150-46-8 --> |
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|StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| PubChem = 635956 |
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|StdInChI = 1S/2C17H14P.Fe/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; |
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| SMILES = C1=CC=C(C=C1)P(2C=CC=C2)C3=CC=CC=C3 .C1=CC=C(C=C1)P(2C=CC=C2)C3=CC=CC=C3. |
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|StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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}} |
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|StdInChIKey = HPXNTHKXCYMIJL-UHFFFAOYSA-N |
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| Section2 = {{Chembox Properties |
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|CASNo_Ref = {{cascite|correct|chemspider}} |
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| Formula = C<sub>34</sub>H<sub>28</sub>FeP<sub>2</sub> |
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|CASNo = 12150-46-8 |
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| MolarMass = 554.391 |
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|UNII_Ref = {{fdacite|correct|FDA}} |
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| Appearance = |
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|UNII = L7Z23UWS3H |
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| Density = |
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|PubChem = 635956 |
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| MeltingPt = 181-183 °C |
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|SMILES1 = c1ccc(cc1)P(c2ccccc2)C34C53678912(C5C6C74)C3C8C9C1(C23)P(c1ccccc1)c1ccccc1 |
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| BoilingPt = |
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|SMILES2 = C1=CC=C(C=C1)P(2C=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(2C=CC=C2)C3=CC=CC=C3. |
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| Solubility = |
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}} |
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| Section3 = {{Chembox Hazards |
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| MainHazards = Toxic |
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| FlashPt = |
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| Autoignition = |
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| RPhrases = {{R25}} |
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| SPhrases = {{S28}}A {{S45}} |
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}} |
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}} |
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}} |
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|Section2={{Chembox Properties |
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|Formula = C{{sub|34}}H{{sub|28}}FeP{{sub|2}} |
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|MolarMass = 554.391 |
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|MeltingPtC = 181 to 183 |
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}} |
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|Section3={{Chembox Hazards |
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|MainHazards = Toxic |
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|GHSPictograms = {{GHS07}}{{GHS08}} |
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|GHSSignalWord = Warning |
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|HPhrases = {{H-phrases|302|312|315|319|332}} |
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}} |
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}} |
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'''1,1{{prime}}-Bis(diphenylphosphino)ferrocene''', commonly abbreviated dppf, is an ] commonly used as a ] in ]. It contains a ] moiety in its backbone, and is related to other bridged ] such as ] (dppe). |
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==Preparation== |
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This compound is commercially available. It may be prepared by treating ] with ]:<ref>{{cite book | chapter = 3.15 The Use of Organolithium Reagents in the Preparation of Ferrocene Derivatives | author = Ian R. Butler | editor = J. Derek Woollins | year = 2010 | isbn = 978-3-527-32472-9 | title = Inorganic Experiments | pages = 175–179 | publisher = John Wiley & Sons | chapter-url = https://books.google.com/books?id=IlL_qLqj_nUC&pg=PA173 | chapter-format = ] excerpt}}</ref> |
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:Fe(C{{sub|5}}H{{sub|4}}Li){{sub|2}} + 2 ClPPh{{sub|2}} → Fe(C{{sub|5}}H{{sub|4}}PPh{{sub|2}}){{sub|2}} + 2 LiCl |
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The dilithiation of ] is easily achieved with ] in the presence of ]. Many related ligands can be made in this way. The Fe center is typically not involved in the behavior of the ligand. |
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==Reactions== |
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Dppf readily forms metal complexes.<ref name = nataro/> The palladium derivative, ], which is popular for ], is prepared by treating dppf with the acetonitrile or benzonitrile adducts of ]:<ref name = nataro>{{cite journal | last1 = Nataro | first1 = Chip | last2 = Fosbenner | first2 = Stephanie M. | title = Synthesis and Characterization of Transition-Metal Complexes Containing 1,1{{prime}}-Bis(diphenylphosphino)ferrocene | journal = ] | volume = 86 | pages = 1412 | year = 2009 | doi = 10.1021/ed086p1412 | issue = 12| bibcode = 2009JChEd..86.1412N }}</ref> Substitution of the phenyl substituents in dppf leads to derivatives with modified donor-acceptor properties at the phosphorus atoms.<ref >{{cite journal | last1 = Dey | first1 = Subhayan | last2 = Pietschnig| first2 = Rudolf | title = Chemistry of sterically demanding dppf-analogs | journal = Coord. Chem. Rev. | volume = 437 | pages = 213850 | year = 2021 | doi = 10.1016/j.ccr.2021.213850 | doi-access = free}}</ref> |
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:dppf + PdCl{{sub|2}}(RCN){{sub|2}} → (dppf)PdCl{{sub|2}} + 2 RCN (RCN = ] or ]) |
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]{{clear left}} |
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Another example of dppf in homogeneous catalysis is provided by the air- and moisture-stable Ni(II) precatalyst [(dppf)Ni(cinnamyl)Cl. It promotes Suzuki-Miyuara cross-coupling of heteroaryl boronic acids with nitrogen- and sulfur-containing heteroaryl halides.<ref>{{Cite journal |last1=Ge |first1=Shaozhong |last2=Hartwig |first2=John F. |date=2012-12-14 |title=Highly Reactive, Single-Component Nickel Catalyst Precursor for Suzuki–Miyuara Cross-Coupling of Heteroaryl Boronic Acids with Heteroaryl Halides |journal=Angewandte Chemie International Edition |language=en |volume=51 |issue=51 |pages=12837–12841 |doi=10.1002/anie.201207428 |pmc=3613336 |pmid=23136047}}</ref> |
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Another dppf-based catalyst is (dppf)Ni(''o''-tolyl)Cl, can be prepared from ligand exchange with (PPh<sub>3</sub>)<sub>2</sub>Ni(''o''-tolyl)Cl. It promotes the amination of aryl chlorides, sulfamates, mesylates, and triflates.<ref>{{Cite journal |last1=Park |first1=Nathaniel H. |last2=Teverovskiy |first2=Georgiy |last3=Buchwald |first3=Stephen L. |date=2014-01-03 |title=Development of an Air-Stable Nickel Precatalyst for the Amination of Aryl Chlorides, Sulfamates, Mesylates, and Triflates |journal=Organic Letters |volume=16 |issue=1 |pages=220–223 |doi=10.1021/ol403209k |pmc=3926134 |pmid=24283652}}</ref> |
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==See also== |
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* ] |
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* ] catalysis |
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==References== |
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{{reflist}} |
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{{DEFAULTSORT:Bisdiphenylphosphinoferrocene, 1, 1'-}} |
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] |
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] |
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] |