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<title>Metal-phosphine complex</title>

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Metal-phosphine complex

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<div id="mw-content-text" class="mw-body-content mw-content-ltr" lang="en" dir="ltr"><div class="mw-content-ltr mw-parser-output" lang="en" dir="ltr">A metal-phosphine complex is a <a href="Coordination_complex" title="Coordination complex">coordination complex</a> containing one or more phosphine ligands. Almost always, the phosphine is an <a href="Organophosphine" title="Organophosphine">organophosphine</a> of the type R3P (R = alkyl, aryl). Metal phosphine complexes are useful in <a href="Homogeneous_catalysis" title="Homogeneous catalysis">homogeneous catalysis</a>.<a href="#cite_note-1">[1]</a><a href="#cite_note-2">[2]</a> Prominent examples of metal phosphine complexes include <a href="Wilkinson's_catalyst" title="Wilkinson's catalyst">Wilkinson's catalyst</a> (Rh(PPh3)3Cl), <a href="Grubbs'_catalyst" class="mw-redirect" title="Grubbs' catalyst">Grubbs' catalyst</a>, and <a href="Tetrakis(triphenylphosphine)palladium(0)" title="Tetrakis(triphenylphosphine)palladium(0)">tetrakis(triphenylphosphine)palladium(0)</a>.<a href="#cite_note-3">[3]</a>

<div class="mw-heading mw-heading2"><h2 id="Preparation">Preparation</h2></div>

Many metal phosphine complexes are prepared by reactions of metal halides with preformed phosphines. For example, treatment of a suspension of <a href="Palladium_chloride" class="mw-redirect" title="Palladium chloride">palladium chloride</a> in ethanol with triphenylphosphine yields monomeric <a href="Bis(triphenylphosphine)palladium(II)_chloride" class="mw-redirect" title="Bis(triphenylphosphine)palladium(II) chloride">bis(triphenylphosphine)palladium(II) chloride</a> units.<a href="#cite_note-4">[4]</a>

The first reported phosphine complexes were cis- and trans-PtCl2(PEt3)2 reported by Cahours and Gal in 1870.<a href="#cite_note-McAuliffe-5">[5]</a>

Often the phosphine serves both as a ligand and as a reductant. This property is illustrated by the synthesis of many platinum-metal complexes of <a href="Triphenylphosphine" title="Triphenylphosphine">triphenylphosphine</a>:<a href="#cite_note-IS-6">[6]</a>

<div class="mw-heading mw-heading2"><h2 id="M-PR3_bonding">M-PR3 bonding</h2></div>

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</style><div role="note" class="hatnote navigation-not-searchable">See also: <a href="%CE%A0-backbonding" class="mw-redirect" title="Π-backbonding">π-backbonding</a></div>

Phosphines are <a href="L-type_ligand" class="mw-redirect" title="L-type ligand">L-type ligands</a>. Unlike most <a href="Metal_ammine_complex" title="Metal ammine complex">metal ammine complexes</a>, metal phosphine complexes tend to be <a href="Lipophilic" class="mw-redirect" title="Lipophilic">lipophilic</a>, displaying good <a href="Solubility" title="Solubility">solubility</a> in <a href="Organic_solvent" class="mw-redirect" title="Organic solvent">organic solvents</a>.

<caption>TEP for selected phosphines<a href="#cite_note-Tolman-7">[7]</a> (A1 mode of Ni(CO)3L in CH2Cl2)

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<th>ν(CO) cm−1

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<td>2056.1

</td></tr>

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<td>2064.1

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<td>2068.9

</td></tr>

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<td>2076.3

</td></tr>

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<td>2097.0

</td></tr>

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<td>2110.8

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Phosphine ligands are also π-acceptors. Their <a href="Pi_acidity" class="mw-redirect" title="Pi acidity">π-acidity</a> arises from overlap of P-C σ* <a href="Anti-bonding_orbital" class="mw-redirect" title="Anti-bonding orbital">anti-bonding orbitals</a> with filled metal orbitals. Aryl- and fluorophosphines are stronger π-acceptors than alkylphosphines. <a href="Trifluorophosphine" class="mw-redirect" title="Trifluorophosphine">Trifluorophosphine</a> (PF3) is a strong π-acid with bonding properties akin to those of the <a href="Carbonyl_ligand" class="mw-redirect" title="Carbonyl ligand">carbonyl ligand</a>.<a href="#cite_note-8">[8]</a> In early work, phosphine ligands were thought to utilize 3<a href="D_orbital" class="mw-redirect" title="D orbital">d orbitals</a> to form M-P pi-bonding, but it is now accepted that d-orbitals on phosphorus are not involved in bonding.<a href="#cite_note-9">[9]</a> The energy of the σ* orbitals is lower for phosphines with <a href="Electronegative" class="mw-redirect" title="Electronegative">electronegative</a> <a href="Substituent" title="Substituent">substituents</a>, and for this reason <a href="Phosphorus_trifluoride" title="Phosphorus trifluoride">phosphorus trifluoride</a> is a particularly good π-acceptor.<a href="#cite_note-10">[10]</a>

<div class="gallerytext">R3P–M σ bonding</div>

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<div class="gallerytext">R3P–M π backbonding</div>

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<div class="mw-heading mw-heading3"><h3 id="Steric_properties">Steric properties</h3></div>

In contrast to tertiary phosphines, <a href="Tertiary_amine" class="mw-redirect" title="Tertiary amine">tertiary amines</a>, especially arylamine derivatives, are reluctant to bind to metals. The difference between the coordinating power of PR3 and NR3 reflects the greater steric crowding around the nitrogen atom, which is smaller.

By changes in one or more of the three organic substituents, the <a href="Steric" class="mw-redirect" title="Steric">steric</a> and <a href="Tolman_electronic_parameter" title="Tolman electronic parameter">electronic</a> properties of phosphine ligands can be manipulated.<a href="#cite_note-crabtree-11">[11]</a> The steric properties of phosphine ligands can be ranked by their <a href="Tolman_cone_angle" class="mw-redirect" title="Tolman cone angle">Tolman cone angle</a><a href="#cite_note-Tolman-7">[7]</a> or percent buried volume.<a href="#cite_note-12">[12]</a>

<div class="mw-heading mw-heading3"><h3 id="Spectroscopy">Spectroscopy</h3></div>

An important technique for the characterization of metal-PR3 complexes is <a href="Phosphorus_NMR" class="mw-redirect" title="Phosphorus NMR">31P NMR spectroscopy</a>. Substantial shifts occur upon complexation. 31P-31P spin-spin coupling can provide insight into the structure of complexes containing multiple phosphine ligands.<a href="#cite_note-13">[13]</a><a href="#cite_note-14">[14]</a>

<div class="mw-heading mw-heading2"><h2 id="Reactivity">Reactivity</h2></div>

Phosphine ligands are usually "spectator" rather than "actor" ligands. They generally do not participate in reactions, except to dissociate from the metal center. In certain high temperature <a href="Hydroformylation" title="Hydroformylation">hydroformylation</a> reactions, the scission of P-C bonds is observed however.<a href="#cite_note-15">[15]</a> The thermal stability of phosphines ligands is enhanced when they are incorporated into <a href="Pincer_complex" class="mw-redirect" title="Pincer complex">pincer complexes</a>.

<div class="mw-heading mw-heading2"><h2 id="Applications_to_homogeneous_catalysis">Applications to homogeneous catalysis</h2></div>

One of the first applications of phosphine ligands in catalysis was the use of <a href="Triphenylphosphine" title="Triphenylphosphine">triphenylphosphine</a> in "<a href="Walter_Reppe" title="Walter Reppe">Reppe</a>" chemistry (1948), which included reactions of <a href="Alkyne" title="Alkyne">alkynes</a>, <a href="Carbon_monoxide" title="Carbon monoxide">carbon monoxide</a>, and <a href="Alcohol_(chemistry)" title="Alcohol (chemistry)">alcohols</a>.<a href="#cite_note-16">[16]</a> In his studies, Reppe discovered that this reaction more efficiently produced acrylic esters using NiBr2(<a href="Triphenylphosphine" title="Triphenylphosphine">PPh3</a>)2 as a catalyst instead of <a href="Nickel(II)_bromide" title="Nickel(II) bromide">NiBr2</a>. Shell developed cobalt-based catalysts modified with trialkylphosphine ligands for hydroformylation (now a rhodium catalyst is more commonly used for this process).<a href="#cite_note-17">[17]</a> The success achieved by Reppe and his contemporaries led to many industrial applications.<a href="#cite_note-18">[18]</a>

<div class="mw-heading mw-heading3"><h3 id="Illustrative_PPh3_complexes">Illustrative PPh3 complexes</h3></div>

<ul><li><a href="Tetrakis(triphenylphosphine)palladium(0)" title="Tetrakis(triphenylphosphine)palladium(0)">Tetrakis(triphenylphosphine)palladium(0)</a> is widely used to catalyse C-C coupling reactions in <a href="Organic_synthesis" title="Organic synthesis">organic synthesis</a>, see <a href="Heck_reaction" title="Heck reaction">Heck reaction</a>.</li>

<li><a href="Wilkinson's_catalyst" title="Wilkinson's catalyst">Wilkinson's catalyst</a>, RhCl(PPh3)3 is a square planar Rh(I) complex of historical significance used to <a href="Homogeneous_catalysis" title="Homogeneous catalysis">catalyze</a> the hydrogenation of alkenes.</li>

<li><a href="Vaska's_complex" title="Vaska's complex">Vaska's complex</a>, trans-IrCl(CO)(PPh3)2, is also historically significant; it was used to establish the scope of <a href="Oxidative_addition" title="Oxidative addition">oxidative addition</a> reactions. This early work provided the insights that led to the flowering of the area of <a href="Homogeneous_catalysis" title="Homogeneous catalysis">homogeneous catalysis</a>.</li>

<li><a href="Dichlorobis(triphenylphosphine)nickel(II)" title="Dichlorobis(triphenylphosphine)nickel(II)">NiCl2(PPh3)2</a> is a tetrahedral (<a href="Spin_triplet" class="mw-redirect" title="Spin triplet">spin triplet</a>) complex of Ni(II). In contrast <a href="Bis(triphenylphosphine)palladium_chloride" title="Bis(triphenylphosphine)palladium chloride">PdCl2(PPh3)2</a> is square planar.</li>

<li><a href="Stryker's_reagent" title="Stryker's reagent">Stryker's reagent</a>, [(PPh3)CuH]6, PPh3-stabilized <a href="Transition_metal_hydride" title="Transition metal hydride">transition metal hydride</a> cluster that used as a <a href="Reagent" title="Reagent">reagent</a> for "conjugate reductions".</li>

<li><a href="(Triphenylphosphine)iron_tetracarbonyl" title="(Triphenylphosphine)iron tetracarbonyl">(Triphenylphosphine)iron tetracarbonyl</a> (Fe(CO)4(PPh3)) and <a href="Bis(triphenylphosphine)iron_tricarbonyl" title="Bis(triphenylphosphine)iron tricarbonyl">bis(triphenylphosphine)iron tricarbonyl</a> (Fe(CO)3(PPh3)2).</li></ul>

<div class="mw-heading mw-heading2"><h2 id="Complexes_of_other_organophosphorus_ligands">Complexes of other organophosphorus ligands</h2></div>

The popularity and usefulness of phosphine complexes has led to the popularization of complexes of many related organophosphorus ligands.<a href="#cite_note-McAuliffe-5">[5]</a> Complexes of <a href="Arsine" title="Arsine">arsines</a> have also been widely investigated, but are avoided in practical applications because of concerns about toxicity.

<div class="mw-heading mw-heading3"><h3 id="Complexes_of_primary_and_secondary_phosphines">Complexes of primary and secondary phosphines</h3></div>

Most work focuses on complexes of triorganophosphines, but primary and secondary phosphines, respectively RPH2 and R2PH, also function as ligands. Such ligands are less basic and have small cone angles. These complexes are susceptible to deprotonation leading to phosphido-bridged dimers and <a href="Oligomer" title="Oligomer">oligomers</a>:

<div class="mw-heading mw-heading3"><h3 id="Complexes_of_PRx(OR')3−x">Complexes of PRx(OR')3−x</h3></div>

Nickel(0) complexes of phosphites, e.g., Ni[P(OEt)3]4 are useful catalysts for <a href="Hydrocyanation" title="Hydrocyanation">hydrocyanation</a> of alkenes. Related complexes are known for <a href="Phosphinite" title="Phosphinite">phosphinites</a> (R2P(OR')) and <a href="Phosphonite" title="Phosphonite">phosphonites</a> (RP(OR')2).

<div class="mw-heading mw-heading3"><h3 id="Diphosphine_complexes">Diphosphine complexes</h3></div>

<div role="note" class="hatnote navigation-not-searchable">Main article: <a href="Diphosphines" class="mw-redirect" title="Diphosphines">Diphosphines</a></div>

Due to the <a href="Chelate_effect" class="mw-redirect" title="Chelate effect">chelate effect</a>, ligands with two phosphine groups bind more tightly to metal centers than do two monodentate phosphines. The conformational properties of <a href="Diphosphine" class="mw-redirect" title="Diphosphine">diphosphines</a> makes them especially useful in <a href="Asymmetric_catalysis" class="mw-redirect" title="Asymmetric catalysis">asymmetric catalysis</a>, e.g. <a href="Noyori_asymmetric_hydrogenation" class="mw-redirect" title="Noyori asymmetric hydrogenation">Noyori asymmetric hydrogenation</a>. Several diphosphines have been developed, prominent examples include <a href="1%2C2-bis(diphenylphosphino)ethane" class="mw-redirect" title="1,2-bis(diphenylphosphino)ethane">1,2-bis(diphenylphosphino)ethane</a> (dppe) and <a href="1%2C1'-Bis(diphenylphosphino)ferrocene" title="1,1'-Bis(diphenylphosphino)ferrocene">1,1'-Bis(diphenylphosphino)ferrocene</a>, the <a href="Trans-spanning_ligand" title="Trans-spanning ligand">trans spanning</a> <a href="Xantphos" title="Xantphos">xantphos</a> and <a href="Spanphos" class="mw-redirect" title="Spanphos">spanphos</a>. The complex <a href="Dichloro(1%2C3-bis(diphenylphosphino)propane)nickel" title="Dichloro(1,3-bis(diphenylphosphino)propane)nickel">dichloro(1,3-bis(diphenylphosphino)propane)nickel</a> is useful in <a href="Kumada_coupling" title="Kumada coupling">Kumada coupling</a>.

<div class="mw-heading mw-heading2"><h2 id="References">References</h2></div>

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<li id="cite_note-1"><a href="#cite_ref-1">^</a> Hartwig, J. F. Organotransition Metal Chemistry, from Bonding to Catalysis; University Science Books: New York, 2010. <style data-mw-deduplicate="TemplateStyles:r1238218222">

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</style><a href="ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <bdi>1-891389-53-X</bdi>

</li>

<li id="cite_note-2"><a href="#cite_ref-2">^</a> <cite id="CITEREFPaul_C._J._Kamer,_Piet_W._N._M._van_Leeuwen2012" class="citation book cs1">Paul C. J. Kamer, Piet W. N. M. van Leeuwen, ed. (2012). Phosphorus(III)Ligands in Homogeneous Catalysis: Design and Synthesis. New York: Wiley. <a href="ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <bdi>978-0-470-66627-2</bdi>.</cite>

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<li id="cite_note-3"><a href="#cite_ref-3">^</a> <cite id="CITEREFIaroshenko2019" class="citation book cs1">Iaroshenko, Viktor (4 January 2019). "Phosphines and Related Tervalent Phosphorus Systems". In Van Leeuwen, Piet W. N. M. (ed.). Organophosphorus Chemistry: From Molecules to Applications. pp. 1–58. <a href="Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2F9783527672240.ch1">10.1002/9783527672240.ch1</a>. <a href="ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <bdi>9783527672240</bdi>.</cite>

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<li id="cite_note-4"><a href="#cite_ref-4">^</a> <cite id="CITEREFMiyauraSuzuki1993" class="citation journal cs1"><a href="Norio_Miyaura" title="Norio Miyaura">Miyaura, Norio</a>; <a href="Akira_Suzuki_(chemist)" class="mw-redirect" title="Akira Suzuki (chemist)">Suzuki, Akira</a> (1993). "Palladium-Catalyzed Reaction of 1-Alkenylboronates with Vinylic Halides: (1Z,3E)-1-Phenyl-1,3-octadiene". Org. Synth. 68: 130. <a href="Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.15227%2Forgsyn.068.0130">10.15227/orgsyn.068.0130</a>.</cite>

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<li id="cite_note-McAuliffe-5">^ <a href="#cite_ref-McAuliffe_5-0">a</a> <a href="#cite_ref-McAuliffe_5-1">b</a> <cite id="CITEREFC._A._McAuliffe1973" class="citation book cs1">C. A. McAuliffe, ed. (1973). Transition Metal Complexes of Phosphorus, Arsenic, and Antimony Ligands. J. Wiley. <a href="ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <bdi>0-470-58117-4</bdi>.</cite>

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<li id="cite_note-IS-6"><a href="#cite_ref-IS_6-0">^</a> <cite id="CITEREFOsbornWilkinson1967" class="citation book cs1">Osborn, J. A.; Wilkinson, G. (1967). "Tris(triphenylphosphine)halorhodium(I)". Inorganic Syntheses. Vol. 10. p. 67. <a href="Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2F9780470132418.ch12">10.1002/9780470132418.ch12</a>. <a href="ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <bdi>9780470131695</bdi>.</cite>

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<li id="cite_note-Tolman-7">^ <a href="#cite_ref-Tolman_7-0">a</a> <a href="#cite_ref-Tolman_7-1">b</a> <cite id="CITEREFTolman1977" class="citation journal cs1">Tolman, C. A. (1977). "Steric effects of Phosphorus Ligands in Organometallic Chemistry and Homogeneous Catalysis". <a href="Chemical_Reviews" title="Chemical Reviews">Chemical Reviews</a>. 77 (3): 313–348. <a href="Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fcr60307a002">10.1021/cr60307a002</a>.</cite>

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<li id="cite_note-8"><a href="#cite_ref-8">^</a> <cite id="CITEREFOrpenConnelly1990" class="citation journal cs1">Orpen, A. G.; Connelly, N. G. (1990). "Structural Systematics: the Role of P-A σ* Orbitals in Metal-Phosphorus π-Bonding in Redox-Related Pairs of M-PA3 Complexes (A = R, Ar, OR; R = alkyl)". <a href="Organometallics" title="Organometallics">Organometallics</a>. 9 (4): 1206–1210. <a href="Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fom00118a048">10.1021/om00118a048</a>.</cite>

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<li id="cite_note-9"><a href="#cite_ref-9">^</a> <cite id="CITEREFGilheany1994" class="citation journal cs1">Gilheany, D. G. (1994). "No d Orbitals but Walsh Diagrams and Maybe Banana Bonds: Chemical Bonding in Phosphines, Phosphine Oxides, and Phosphonium Ylides". <a href="Chemical_Reviews" title="Chemical Reviews">Chem. Rev.</a> 94 (5): 1339–1374. <a href="Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fcr00029a008">10.1021/cr00029a008</a>. <a href="PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/27704785">27704785</a>.</cite>

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<li id="cite_note-10"><a href="#cite_ref-10">^</a> <cite id="CITEREFCrabtree2009" class="citation book cs1"><a href="Robert_H._Crabtree" title="Robert H. Crabtree">Crabtree, Robert H.</a> (2009). The Organometallic Chemistry of the Transition Metals (5th ed.). Wiley. pp. 99–100. <a href="ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <bdi>978-0-470-25762-3</bdi>.</cite>

</li>

<li id="cite_note-crabtree-11"><a href="#cite_ref-crabtree_11-0">^</a> <cite id="CITEREFR._H._Crabtree2005" class="citation book cs1">R. H. Crabtree (2005). "4. Carbonyls, Phosphine Complexes, and Ligand Substitution Reactions". <a rel="nofollow" class="external text" href="https://archive.org/details/The_Organometallic_Chemistry_Of_Transition_Metals">The Organometallic Chemistry of the Transition Metals</a> (4th ed.). Wiley. <a href="ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <bdi>0-471-66256-9</bdi>.</cite>

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<li id="cite_note-12"><a href="#cite_ref-12">^</a> <cite id="CITEREFNewman-StonebrakerSmithBorowskiPeters2021" class="citation journal cs1">Newman-Stonebraker, Samuel H.; Smith, Sleight R.; Borowski, Julia E.; Peters, Ellyn; Gensch, Tobias; Johnson, Heather C.; Sigman, Matthew S.; Doyle, Abigail G. (2021). "Univariate classification of phosphine ligation state and reactivity in cross-coupling catalysis". Science. 374 (6565): 301–308. <a href="Bibcode_(identifier)" class="mw-redirect" title="Bibcode (identifier)">Bibcode</a>:<a rel="nofollow" class="external text" href="https://ui.adsabs.harvard.edu/abs/2021Sci...374..301N">2021Sci...374..301N</a>. <a href="Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1126%2Fscience.abj4213">10.1126/science.abj4213</a>. <a href="PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/34648340">34648340</a>. <a href="S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:238991361">238991361</a>.</cite>

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<li id="cite_note-13"><a href="#cite_ref-13">^</a> <cite id="CITEREFNelson2003" class="citation book cs1">Nelson, John H. (2003). Nuclear Magnetic Resonance Spectroscopy. Prentice Hall. <a href="ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <bdi>978-0130334510</bdi>.</cite>

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<li id="cite_note-14"><a href="#cite_ref-14">^</a> <cite id="CITEREFPaul_S._Pregosin,_Roland_W._Kunz2012" class="citation book cs1">Paul S. Pregosin, Roland W. Kunz (2012). 31P and 13C NMR of Transition Metal Phosphine Complexes. Berlin: Springer. <a href="ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <bdi>9783642488306</bdi>.</cite>

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<li id="cite_note-15"><a href="#cite_ref-15">^</a> <cite id="CITEREFGarrou1985" class="citation journal cs1">Garrou, Philip E. (1985). "Transition-Metal-Mediated Phosphorus-Carbon Bond Cleavage and Its Relevance to Homogeneous Catalyst Deactivation". Chem. Rev. 85 (3): 171–185. <a href="Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fcr00067a001">10.1021/cr00067a001</a>.</cite>

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<li id="cite_note-16"><a href="#cite_ref-16">^</a> <cite id="CITEREFReppeSchweckendiek1948" class="citation journal cs1">Reppe, W.; Schweckendiek, W. J. (31 July 1948). "Cyclisierende Polymerisation von Acetylen. III Benzol, Benzolderivate und hydroaromatische Verbindungen". Justus Liebigs Annalen der Chemie. 560 (1): 104–116. <a href="Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2Fjlac.19485600104">10.1002/jlac.19485600104</a>.</cite>

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<li id="cite_note-17"><a href="#cite_ref-17">^</a> <cite id="CITEREFSlaugh,_LMullineaux,_R.1968" class="citation journal cs1">Slaugh, L; Mullineaux, R. (1968). "Novel Hydroformylation catalysts". <a href="J._Organomet._Chem." class="mw-redirect" title="J. Organomet. Chem.">J. Organomet. Chem.</a> 13 (2): 469. <a href="Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2FS0022-328X%2800%2982775-8">10.1016/S0022-328X(00)82775-8</a>.</cite>

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<li id="cite_note-18"><a href="#cite_ref-18">^</a> P. W.N.M. van Leeuwen "Homogeneous Catalysis: Understanding the Art, 2004 Kluwer, Dordrecht. <a href="ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <bdi>1-4020-2000-7</bdi>

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<li id="cite_note-19"><a href="#cite_ref-19">^</a> <cite id="CITEREFHerrmannKohlpaintner1998" class="citation book cs1">Herrmann, W. A.; Kohlpaintner, C. W. (1998). "Syntheses of Water-Soluble Phosphines and their Transition Metal Complexes". Inorganic Syntheses. Vol. 32. pp. 8–25. <a href="Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2F9780470132630.ch2">10.1002/9780470132630.ch2</a>. <a href="ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <bdi>9780471249214</bdi>.</cite> <code class="cs1-code">{{cite book}}</code>: <code class="cs1-code">|journal=</code> ignored (help)

</li>

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</style><div id="Coordination_complexes257" style="font-size:114%;margin:0 4em"><a href="Coordination_complex" title="Coordination complex">Coordination complexes</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="Hydrogen" title="Hydrogen">H</a> donors:</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em">

</div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="Boron" title="Boron">B</a> donors:</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em">

</div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="Carbon" title="Carbon">C</a> donors:</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em">

</div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="Silicon" title="Silicon">Si</a> donors:</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em">

<ul><li><a href="Transition_metal_silane_complexes" class="mw-redirect" title="Transition metal silane complexes">HnSiR4−n</a></li>

</div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="Nitrogen" title="Nitrogen">N</a> donors:</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em">

<li><a href="Transition_metal_imidazole_complex" title="Transition metal imidazole complex">imidazole</a></li>

<li><a href="Transition_metal_amino_acid_complexes" title="Transition metal amino acid complexes">amino acid</a></li>

<li><a href="Transition_metal_porphyrin_complexes" title="Transition metal porphyrin complexes">porphyrin</a></li>

</div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="Phosphorus" title="Phosphorus">P</a> donors:</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em">

</div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="Arsenic" title="Arsenic">As</a> donors:</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em">

</div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="Bismuth" title="Bismuth">Bi</a> donors:</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em">

<ul><li><a href="Bismuth_organometallic_chemistry" title="Bismuth organometallic chemistry">RnBin</a></li>

</div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="Oxygen" title="Oxygen">O</a> donors:</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em">

<li><a href="Transition_metal_carboxamide_complex" title="Transition metal carboxamide complex">RCONR'2</a></li>

</div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="Sulfur" title="Sulfur">S</a> donors:</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em">

</div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="Halide" title="Halide">Halide</a> donors:</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em">

</div></td></tr></tbody></table></div></div><div><div class="zim-footer">

This article is issued from <a class="external text" title="Last edited on 2024-06-22" href="https://en.wikipedia.org/wiki/?title=Metal-phosphine_complex&oldid=1230435430">Wikipedia</a>. The text is available under <a class="external text" href="https://creativecommons.org/licenses/by-sa/4.0/deed.en">Creative Commons Attribution-Share Alike 4.0</a> unless otherwise noted. Additional terms may apply for the media files.

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