1,1'-Bis(diphenylphosphino)ferrocene

1,1-Bis(diphenylphosphino)ferrocene correct changed 477199791 Dppfnew.png 150px Dppf-from-xtal-3D-balls.png 250px (Ferrocene-1,1-diyl)bis(diphenylphosphane) 1,1-Bis(diphenylphosphino)ferrocene, 1,1-ferrocenediylbis(diphenylphosphine), Dppf, 1,1-ferrocenebis(diphenylphosphine), 1,1-bis(diphenylphosphanyl)ferrocene correct chemspider correct EBI 30743 21865114 640-119-0 24075 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 HPXNTHKXCYMIJL-UHFFFAOYSA-N 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 HPXNTHKXCYMIJL-KDKHWAOJAX correct chemspider 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; correct chemspider HPXNTHKXCYMIJL-UHFFFAOYSA-N correct chemspider 12150-46-8 correct FDA L7Z23UWS3H 635956 c1ccc(cc1)P(c2ccccc2)C34C5[Fe]3678912(C5C6C74)C3C8C9C1(C23)P(c1ccccc1)c1ccccc1 C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.[Fe+2] C34H28FeP2 554.391 181 to 183 Toxic 07 08 Warning 302 312 315 319 332 1,1-Bis(diphenylphosphino)ferrocene, commonly abbreviated dppf, is an organophosphorus compound commonly used as a ligand in homogeneous catalysis. It contains a ferrocene moiety in its backbone, and is related to other bridged diphosphines such as 1,2-bis(diphenylphosphino)ethane (dppe). Preparation This compound is commercially available. It may be prepared by treating dilithioferrocene with chlorodiphenylphosphine: 3.15 The Use of Organolithium Reagents in the Preparation of Ferrocene Derivatives Ian R. Butler J. Derek Woollins 2010 978-3-527-32472-9 Inorganic Experiments 175–179 John Wiley & Sons https://books.google.com/books?id=IlL_qLqj_nUC&pg=PA173 Google Books excerpt Fe(C5H4Li)2 + 2 ClPPh2 → Fe(C5H4PPh2)2 + 2 LiCl The dilithiation of ferrocene is easily achieved with n-butyllithium in the presence of TMEDA. Many related ligands can be made in this way. The Fe center is typically not involved in the behavior of the ligand. Reactions Dppf readily forms metal complexes. The palladium derivative, (dppf)PdCl2, which is popular for palladium-catalyzed coupling reactions, is prepared by treating dppf with the acetonitrile or benzonitrile adducts 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 2009 10.1021/ed086p1412 12 2009JChEd..86.1412N Substitution of the phenyl substituents in dppf leads to derivatives with modified donor-acceptor properties at the phosphorus atoms. Dey Subhayan Pietschnig Rudolf Chemistry of sterically demanding dppf-analogs Coord. Chem. Rev. 437 213850 2021 10.1016/j.ccr.2021.213850 free dppf + PdCl2(RCN)2 → (dppf)PdCl2 + 2 RCN (RCN = acetonitrile or benzonitrile) thumb|left|150px|Structure of the complex PtCl2(dppf) 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.Ge Shaozhong Hartwig John F. 2012-12-14 Highly Reactive, Single-Component Nickel Catalyst Precursor for Suzuki–Miyuara Cross-Coupling of Heteroaryl Boronic Acids with Heteroaryl Halides Angewandte Chemie International Edition en 51 51 12837–12841 10.1002/anie.201207428 3613336 23136047 center|478x478px|thumb|Synthesis of [(dppf)Ni(cinnamyl)Cl)] Another dppf-based catalyst is (dppf)Ni(o-tolyl)Cl, can be prepared from ligand exchange with (PPh3)2Ni(o-tolyl)Cl. It promotes the amination of aryl chlorides, sulfamates, mesylates, and triflates.Park Nathaniel H. Teverovskiy Georgiy Buchwald Stephen L. 2014-01-03 Development of an Air-Stable Nickel Precatalyst for the Amination of Aryl Chlorides, Sulfamates, Mesylates, and Triflates Organic Letters 16 1 220–223 10.1021/ol403209k 3926134 24283652 center|253x253px|thumb|Synthesis of (dppf)Ni(o-tolyl)Cl See also Diphosphines borrowing hydrogen catalysis References Category:Ferrocenes Category:Tertiary phosphines Category:Diphosphines