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Four lithium atoms (in purple) form a [[tetrahedron]], with four [[butyl]] groups attached to the faces (carbon is black, hydrogen is white).]] '''Organometallic chemistry''' is the study of '''organometallic compounds''', [[chemical compound]]s containing at least one [[chemical bond]] between a [[carbon]] atom of an [[organic molecule]] and a [[metal]], including [[alkali]], [[alkaline earth]], and [[transition metals]], and sometimes broadened to include [[metalloids]] like boron, silicon, and selenium, as well.{{sfn|Crabtree|2009|p={{pn|date=October 2021}}}}<ref name=":0">{{GoldBookRef |title=organometallic compounds |file=O04328 }}</ref> Aside from bonds to [[organyl]] fragments or molecules, bonds to 'inorganic' carbon, like [[carbon monoxide]] ([[Metal carbonyl|metal carbonyls]]), [[cyanide]], or [[carbide]], are generally considered to be organometallic as well. Some related compounds such as [[transition metal hydride]]s and [[metal phosphine complexes]] are often included in discussions of organometallic compounds, though strictly speaking, they are not necessarily organometallic. The related but distinct term "[[metalorganics|metalorganic compound]]" refers to metal-containing compounds lacking direct metal-carbon bonds but which contain organic ligands. Metal β-diketonates, [[alkoxide]]s, dialkylamides, and metal phosphine complexes are representative members of this class. The field of organometallic chemistry combines aspects of traditional [[inorganic chemistry|inorganic]] and [[organic chemistry]].<ref name=ChrisE>{{cite book|title=Organometallics|author=C. Elschenbroich|publisher=VCH|year=2006|isbn= 978-3-527-29390-2}}</ref> Organometallic compounds are widely used both stoichiometrically in research and industrial chemical reactions, as well as in the role of catalysts to increase the rates of such reactions (e.g., as in uses of [[homogeneous catalysis]]), where target molecules include polymers, pharmaceuticals, and many other types of practical products. == Organometallic compounds == [[File:Magnesium bis-cyclopentadienyl bottle.jpg|180px|thumb|right|A steel bottle containing MgCp<sub>2</sub> [[magnesocene|(magnesium bis-cyclopentadienyl)]], which, like several other organometallic compounds, is pyrophoric in air.]] Organometallic compounds are distinguished by the prefix "organo-" (e.g., organopalladium compounds), and include all compounds which contain a bond between a metal atom and a carbon atom of an [[organyl group]].<ref name=":0" /> In addition to the traditional metals ([[alkali metal]]s, [[alkali earth metal]]s, [[transition metals]], and [[post transition metals]]), [[lanthanide]]s, [[actinide]]s, semimetals, and the elements [[boron]], [[silicon]], [[arsenic]], and [[selenium]] are considered to form organometallic compounds.<ref name=":0" /> Examples of organometallic compounds include [[Gilman reagent]]s, which contain [[lithium]] and [[copper]], and [[Grignard reagent]]s, which contain [[magnesium]]. Boron-containing organometallic compounds are often the result of [[hydroboration]] and [[carboboration]] reactions. [[Tetracarbonyl nickel]] and [[ferrocene]] are examples of organometallic compounds containing [[transition metal]]s. Other examples of organometallic compounds include [[organolithium]] compounds such as [[n-butyllithium|''n''-butyllithium]] (n-BuLi), [[organozinc]] compounds such as [[diethylzinc]] (Et<sub>2</sub>Zn), [[organotin]] compounds such as [[tributyltin hydride]] (Bu<sub>3</sub>SnH), [[organoborane]] compounds such as [[triethylborane]] (Et<sub>3</sub>B), and [[organoaluminium]] compounds such as [[trimethylaluminium]] (Me<sub>3</sub>Al).<ref name=ChrisE/> A naturally occurring organometallic complex is [[methylcobalamin]] (a form of [[Vitamin B12|Vitamin B<sub>12</sub>]]), which contains a [[cobalt]]-[[methyl]] bond. This complex, along with other biologically relevant complexes are often discussed within the subfield of [[bioorganometallic chemistry]].{{sfn|Lippard|Berg|1994|p={{pn|date=October 2021}}}} <gallery widths="140" heights="96" caption="Representative Organometallic Compounds"> File:Ferrocene.svg|[[Ferrocene]] is an archetypal organoiron complex. It is an air-stable, sublimable compound. File:Cobaltocene.svg|[[Cobaltocene]] is a structural analogue of ferrocene, but is highly reactive toward air. File:HRh(CO)P3again.png|[[Tris(triphenylphosphine)rhodium carbonyl hydride]] is used in the commercial production of many aldehyde-based [[fragrance]]s. File:Zeise'sSalt.png|[[Zeise's salt]] is an example of a [[transition metal alkene complex]]. File:Trimethylaluminium-from-xtal-3D-bs-17.png|[[Trimethylaluminium]] is an organometallic compound with a [[Bridging ligand|bridging]] [[methyl group]]. It is used in the industrial production of some alcohols. File:Dimethylzinc-3D-balls.png|[[Dimethylzinc]] has a linear coordination. It is a volatile pyrophoric liquid that is used in the preparation of semiconducting films. File:Lithium-diphenylcuprate-etherate-dimer-from-xtal-2D-skeletal.png|Lithium diphenylcuprate bis(diethyl etherate) is an example of a [[Gilman reagent]], a type of organocopper complex frequently employed in organic synthesis. File:AdoCbl-ColorCoded.png|[[Adenosylcobalamin]] is a [[Cofactor (biochemistry)|cofactor]] required by several crucial enzymatic reactions that take place in the human body. It is a rare example of a metal (cobalt) alkyl in biology. File:IronPentacarbonylStructure.png|[[Iron pentacarbonyl|Iron(0) pentacarbonyl]] is a red-orange liquid prepared directly from the union of finely divided iron and carbon monoxide gas under pressure. File:Tc99 sestamibi 2D structure.svg|[[Technetium (99mTc) sestamibi|Technetium[<sup>99m</sup>Tc] sestamibi]] is used to image the heart muscle in nuclear medicine. </gallery> ===Distinction from coordination compounds with organic ligands=== Many [[Complex (chemistry)|complex]]es feature [[coordination bond]]s between a metal and organic [[ligands]]. Complexes where the organic ligands bind the metal through a [[heteroatom]] such as oxygen or nitrogen are considered coordination compounds (e.g., [[heme A]] and [[Tris(acetylacetonato)iron(III)|Fe(acac)<sub>3</sub>]]). However, if any of the ligands form a direct metal-carbon (M-C) bond, then the complex is considered to be organometallic. Although the IUPAC has not formally defined the term, some chemists use the term "metalorganic" to describe any coordination compound containing an organic ligand regardless of the presence of a direct M-C bond.<ref>{{cite book |doi=10.1016/B978-0-12-409547-2.13135-X |chapter=Metalorganic Functionalization in Vacuum |title=Encyclopedia of Interfacial Chemistry |year=2018 |last1=Rodríguez-Reyes |first1=J.C.F. |last2=Silva-Quiñones |first2=D. |pages=761–768 |isbn=978-0-12-809894-3 }}</ref> The status of compounds in which the [[resonance (chemistry)|canonical anion]] has a negative charge that is shared between ([[delocalized electrons|delocalized]]) a carbon atom and an atom more [[electronegativity|electronegative]] than carbon (e.g. [[enolate]]s) may vary with the nature of the anionic moiety, the metal ion, and possibly the medium. In the absence of direct structural evidence for a carbon–metal bond, such compounds are not considered to be organometallic.<ref name=":0" /> For instance, lithium enolates often contain only Li-O bonds and are not organometallic, while zinc enolates ([[Reformatsky reaction|Reformatsky reagents]]) contain both Zn-O and Zn-C bonds, and are organometallic in nature.<ref name=ChrisE/> ===Structure and properties=== The metal-carbon bond in organometallic compounds is generally highly [[covalent]].{{sfn|Crabtree|2009|p={{pn|date=October 2021}}}} For highly electropositive elements, such as lithium and sodium, the carbon ligand exhibits [[carbanion]]ic character, but free carbon-based anions are extremely rare, an example being [[cyanide]]. [[File:Mn(II) kompleksi monokoristall.jpg|thumb|a single crystal of a Mn(II) complex, [BnMIm]4[MnBr4]Br2. Its bright green color originates from spin-forbidden d-d transitions]] Most organometallic compounds are solids at room temperature, however some are liquids such as [[methylcyclopentadienyl manganese tricarbonyl]], or even [[volatility (chemistry)|volatile]] liquids such as [[nickel tetracarbonyl]].{{sfn|Crabtree|2009|p={{pn|date=October 2021}}}} Many organometallic compounds are [[Air sensitivity|air sensitive]] (reactive towards oxygen and moisture), and thus they must be handled under an [[Inert gas|inert atmosphere]].{{sfn|Crabtree|2009|p={{pn|date=October 2021}}}} Some organometallic compounds such as [[triethylaluminium]] are [[Pyrophoricity|pyrophoric]] and will [[Combustion|ignite]] on contact with air.<ref>{{Cite web|last=|first=|date=2016-05-24|title=Triethylaluminium – SDS|url=https://www.chemblink.com/MSDS/MSDSFiles/97-93-8_Sigma-Aldrich.pdf|archive-url=https://web.archive.org/web/20220125201058/https://www.chemblink.com/MSDS/MSDSFiles/97-93-8_Sigma-Aldrich.pdf|archive-date=25 January 2022|access-date=2021-01-03|website=chemBlink|url-status=dead}}</ref> ==Concepts and techniques== As in other areas of chemistry, [[electron counting]] is useful for organizing organometallic chemistry. The [[18-electron rule]] is helpful in predicting the stabilities of organometallic complexes, for example [[metal carbonyl]]s and [[Transition metal hydride|metal hydrides]]. The 18e rule has two representative electron counting models, ionic and neutral (also known as covalent) ligand models, respectively.<ref name=":02">{{Cite book |last=Crabtree |first=Robert H. |url=https://www.worldcat.org/oclc/863383849 |title=The organometallic chemistry of the transition metals |date=2014 |isbn=978-1-118-78824-0 |edition=6 |location=Hoboken, New Jersey |pages=43, 44, 205 |oclc=863383849}}</ref> The hapticity of a metal-ligand complex, can influence the electron count.<ref name=":02" /> [[Hapticity]] (η, lowercase Greek eta), describes the number of contiguous ligands coordinated to a metal.<ref name=":02" /> For example, [[ferrocene]], [(η<sup>5</sup>-C<sub>5</sub>H<sub>5</sub>)<sub>2</sub>Fe], has two [[cyclopentadienyl ligand]]s giving a hapticity of 5, where all five carbon atoms of the C<sub>5</sub>H<sub>5</sub> ligand bond equally and contribute one electron to the iron center. Ligands that bind non-contiguous atoms are denoted the Greek letter kappa, κ.<ref name=":02" /> [[Chelation|Chelating]] κ2-acetate is an example. The [[covalent bond classification method]] identifies three classes of ligands, X,L, and Z; which are based on the electron donating interactions of the ligand. Many organometallic compounds do not follow the 18e rule. The metal atoms in organometallic compounds are frequently described by their [[d electron count]] and [[oxidation state]]. These concepts can be used to help predict their reactivity and preferred [[Molecular geometry|geometry]]. Chemical bonding and reactivity in organometallic compounds is often discussed from the perspective of the [[isolobal principle]]. A wide variety of physical techniques are used to determine the structure, composition, and properties of organometallic compounds. [[X-ray diffraction]] is a particularly important technique that can locate the positions of atoms within a solid compound, providing a detailed description of its structure.{{sfn|Crabtree|2009|p={{pn|date=October 2021}}}}{{sfn|Shriver|Weller|Overton|Armstrong|2014|p={{pn|date=October 2021}}}} Other techniques like [[infrared spectroscopy]] and [[nuclear magnetic resonance spectroscopy]] are also frequently used to obtain information on the structure and bonding of organometallic compounds.{{sfn|Crabtree|2009|p={{pn|date=October 2021}}}}{{sfn|Shriver|Weller|Overton|Armstrong|2014|p={{pn|date=October 2021}}}} [[Ultraviolet-visible spectroscopy]] is a common technique used to obtain information on the electronic structure of organometallic compounds. It is also used monitor the progress of organometallic reactions, as well as determine their [[Chemical kinetics|kinetics]].{{sfn|Shriver|Weller|Overton|Armstrong|2014|p={{pn|date=October 2021}}}} The dynamics of organometallic compounds can be studied using [[dynamic NMR spectroscopy]].{{sfn|Crabtree|2009|p={{pn|date=October 2021}}}} Other notable techniques include [[X-ray absorption spectroscopy]],<ref>{{cite journal |last1=Nelson |first1=Ryan C. |last2=Miller |first2=Jeffrey T. |title=An introduction to X-ray absorption spectroscopy and its in situ application to organometallic compounds and homogeneous catalysts |journal=Catal. Sci. Technol. |date=2012 |volume=2 |issue=3 |pages=461–470 |doi=10.1039/C2CY00343K }}</ref> [[electron paramagnetic resonance spectroscopy]], and [[elemental analysis]].{{sfn|Crabtree|2009|p={{pn|date=October 2021}}}}{{sfn|Shriver|Weller|Overton|Armstrong|2014|p={{pn|date=October 2021}}}} Due to their high reactivity towards oxygen and moisture, organometallic compounds often must be handled using [[air-free techniques]]. Air-free handling of organometallic compounds typically requires the use of laboratory apparatuses such as a [[glovebox]] or [[Schlenk line]].{{sfn|Crabtree|2009|p={{pn|date=October 2021}}}} == History == Early developments in organometallic chemistry include [[Louis Claude Cadet de Gassicourt|Louis Claude Cadet]]'s synthesis of methyl arsenic compounds related to [[cacodyl]], [[William Christopher Zeise]]'s<ref>{{cite journal |last1=Hunt |first1=L. B. |title=The First Organometallic Compounds |journal=Platinum Metals Review |date=1 April 1984 |volume=28 |issue=2 |pages=76–83 |citeseerx=10.1.1.693.9965 }}</ref> [[Zeise's salt|platinum-ethylene complex]],<ref>{{cite journal |last1=Zeise |first1=W. C. |title=Von der Wirkung zwischen Platinchlorid und Alkohol, und von den dabei entstehenden neuen Substanzen |trans-title=About the effect between platinum chloride and alcohol, and about the new substances that are created in the process |language=de |journal=Annalen der Physik und Chemie |date=1831 |volume=97 |issue=4 |pages=497–541 |doi=10.1002/andp.18310970402 |bibcode=1831AnP....97..497Z |url=https://zenodo.org/record/1423546 }}</ref> [[Edward Frankland]]'s discovery of [[Diethylzinc|diethyl-]] and [[dimethyl zinc|dimethylzinc]], [[Ludwig Mond]]'s discovery of [[tetracarbonyl nickel|Ni(CO)<sub>4</sub>]],{{sfn|Crabtree|2009|p={{pn|date=October 2021}}}} and [[Victor Grignard]]'s organomagnesium compounds. (Although not always acknowledged as an organometallic compound, [[Prussian blue]], a mixed-valence iron-cyanide complex, was first prepared in 1706 by paint maker [[Johann Jacob Diesbach]] as the first [[coordination polymer]] and synthetic material containing a metal-carbon bond.{{sfn|Crabtree|2009|p=98}}) The abundant and diverse products from coal and petroleum led to [[Ziegler–Natta]], [[Fischer–Tropsch]], [[hydroformylation]] catalysis which employ CO, H<sub>2</sub>, and alkenes as feedstocks and ligands. Recognition of organometallic chemistry as a distinct subfield culminated in the Nobel Prizes to [[Ernst Otto Fischer|Ernst Fischer]] and [[Geoffrey Wilkinson]] for work on [[metallocene]]s. In 2005, [[Yves Chauvin]], [[Robert H. Grubbs]] and [[Richard R. Schrock]] shared the Nobel Prize for metal-catalyzed [[olefin metathesis]].<ref>{{cite journal |last1=Dragutan |first1=V. |last2=Dragutan |first2=I. |last3=Balaban |first3=A. T. |title=2005 Nobel Prize in Chemistry |journal=Platinum Metals Review |date=1 January 2006 |volume=50 |issue=1 |pages=35–37 |doi=10.1595/147106706X94140 |doi-access=free }}</ref> === Organometallic chemistry timeline === * 1760 [[Louis Claude Cadet de Gassicourt]] isolates the [[organoarenic compound]] [[cacodyl]] * 1827 [[William Christopher Zeise]] produces [[Zeise's salt]]; the first [[platinum]] / [[olefin]] complex * 1848 [[Edward Frankland]] discovers [[diethylzinc]] * 1890 [[Ludwig Mond]] discovers [[nickel carbonyl]] * 1899 [[John Ulric Nef (chemist)|John Ulric Nef]] discovers [[alkynylation]] using sodium [[acetylide]]s. * 1909 [[Paul Ehrlich]] introduces [[Salvarsan]] for the treatment of syphilis, an early arsenic based organometallic compound * 1912 [[Nobel Prize in Chemistry|Nobel Prize]] [[Victor Grignard]] and [[Paul Sabatier (chemist)|Paul Sabatier]] * 1930 [[Henry Gilman]] invents lithium cuprates, see [[Gilman reagent]] * 1940 [[Eugene G. Rochow]] and [[Richard Müller (chemist)|Richard Müller]] discover the [[direct process]] for preparing [[organosilicon]] compounds * 1930's and 1940's [[Otto Roelen]] and [[Walter Reppe]] develop metal-catalyzed [[hydroformylation]] and acetylene chemistry * 1951 [[Walter Hieber]] was awarded the [[Alfred Stock]] prize for his work with [[metal carbonyl]] chemistry. * 1951 [[Ferrocene]] is discovered * 1956 [[Dorothy Hodgkin|Dorothy Crawfoot Hodgkin]] determines the structure of [[vitamin B12|vitamin B<sub>12</sub>]], the first biomolecule found to contain a metal-carbon bond, see [[bioorganometallic chemistry]] * 1963 [[Nobel Prize in Chemistry|Nobel prize]] for [[Karl Ziegler]] and [[Giulio Natta]] on [[Ziegler–Natta catalyst]] * 1973 [[Nobel Prize in Chemistry|Nobel prize]] [[Geoffrey Wilkinson]] and [[Ernst Otto Fischer]] on [[sandwich compound]]s * 1981 [[Nobel Prize in Chemistry|Nobel prize]] [[Roald Hoffmann]] and [[Kenichi Fukui]] for creation of the Woodward-Hoffman Rules * 2001 [[Nobel Prize in Chemistry|Nobel prize]] [[W. S. Knowles]], [[R. Noyori]] and [[Karl Barry Sharpless]] for asymmetric hydrogenation * 2005 [[Nobel Prize in Chemistry|Nobel prize]] [[Yves Chauvin]], [[Robert Grubbs]], and [[Richard Schrock]] on metal-catalyzed [[olefin metathesis|alkene metathesis]] * 2010 [[Nobel Prize in Chemistry|Nobel prize]] [[Richard F. Heck]], [[Ei-ichi Negishi]], [[Akira Suzuki (chemist)|Akira Suzuki]] for palladium catalyzed cross coupling reactions ==Scope== Subspecialty areas of organometallic chemistry include: * [[Period 2 element]]s: [[organolithium chemistry]], [[organoberyllium chemistry]], [[organoborane chemistry]] * [[Period 3 element]]s: [[organosodium chemistry]], [[organomagnesium chemistry]], [[organoaluminium chemistry]], [[Organosilicon|organosilicon chemistry]] * [[Period 4 element]]s: [[organocalcium chemistry]], [[organoscandium chemistry]], [[organotitanium chemistry]], [[organovanadium chemistry]], [[organochromium chemistry]], [[organomanganese chemistry]], [[organoiron chemistry]], [[organocobalt chemistry]], [[organonickel chemistry]], [[organocopper chemistry]], [[organozinc chemistry]], [[organogallium chemistry]], [[organogermanium chemistry]], [[organoarsenic chemistry]], [[organoselenium chemistry]] * [[Period 5 element]]s: [[organoyttrium chemistry]], [[organozirconium chemistry]], [[organoniobium chemistry]], [[organomolybdenum chemistry]], [[organotechnetium chemistry]], [[organoruthenium chemistry]], [[organorhodium chemistry]], [[organopalladium chemistry]], [[organosilver chemistry]], [[organocadmium chemistry]], [[organoindium chemistry]], [[organotin chemistry]], [[organoantimony chemistry]], [[organotellurium chemistry]] * [[Period 6 element]]s: [[organolanthanide chemistry]], [[organocerium chemistry]], [[organotantalum chemistry]], [[organotungsten chemistry]], [[organorhenium chemistry]], [[organoosmium chemistry]], [[organoiridium chemistry]], [[organoplatinum chemistry]], [[organogold chemistry]], [[Organomercury|organomercury chemistry]], [[organothallium chemistry]], [[organolead chemistry]], [[organobismuth chemistry]], [[organopolonium chemistry]] * [[Period 7 element]]s: [[organoactinide chemistry]], [[organothorium chemistry]], [[organouranium chemistry]], [[organoneptunium chemistry]] ==Industrial applications==  Organometallic compounds find wide use in commercial reactions, both as [[homogeneous catalysis|homogenous catalysts]] and as [[Stoichiometry|stoichiometric reagents]]. For instance, [[organolithium compound|organolithium]], [[organomagnesium]], and [[organoaluminium compound]]s, examples of which are highly basic and highly reducing, are useful stoichiometrically but also catalyze many polymerization reactions.{{sfn|Elschenbroich|2016|p={{pn|date=October 2021}}}} Almost all processes involving carbon monoxide rely on catalysts, notable examples being described as [[carbonylation]]s.<ref name=Ullmann>{{ Ullmann | author1 = W. Bertleff |author2 = M. Roeper |author3 = X. Sava | title = Carbonylation | doi = 10.1002/14356007.a05_217 }}</ref> The production of acetic acid from methanol and carbon monoxide is catalyzed via [[metal carbonyl complex]]es in the [[Monsanto process]] and [[Cativa process]]. Most synthetic aldehydes are produced via [[hydroformylation]]. The bulk of the synthetic alcohols, at least those larger than ethanol, are produced by [[hydrogenation]] of hydroformylation-derived aldehydes. Similarly, the [[Wacker process]] is used in the oxidation of [[ethylene]] to [[acetaldehyde]].{{sfn|Leeuwen|2005|p={{pn|date=October 2021}}}} [[File:ConstrainedGeomCmpx.png|thumb|120px|A constrained geometry organotitanium complex is a precatalyst for olefin polymerization.]] Almost all industrial processes involving [[alkene]]-derived polymers rely on organometallic catalysts. The world's polyethylene and polypropylene are produced via both [[heterogeneous catalysis|heterogeneously]] via [[Ziegler–Natta]] catalysis and homogeneously, e.g., via [[constrained geometry catalyst]]s.<ref>{{cite journal |last1=Klosin |first1=Jerzy |last2=Fontaine |first2=Philip P. |last3=Figueroa |first3=Ruth |title=Development of Group IV Molecular Catalysts for High Temperature Ethylene-α-Olefin Copolymerization Reactions |journal=Accounts of Chemical Research |date=21 July 2015 |volume=48 |issue=7 |pages=2004–2016 |doi=10.1021/acs.accounts.5b00065 |pmid=26151395 |doi-access=free }}</ref> Most processes involving hydrogen rely on metal-based catalysts. Whereas bulk [[hydrogenation]]s (e.g., margarine production) rely on heterogeneous catalysts, for the production of fine chemicals such hydrogenations rely on soluble (homogenous) organometallic complexes or involve organometallic intermediates.<ref name=Rylander>{{Ullmann |last=Rylander |first=Paul N. |title=Hydrogenation and Dehydrogenation |doi=10.1002/14356007.a13_487 }}</ref> Organometallic complexes allow these hydrogenations to be effected asymmetrically. Many [[III-V semiconductor|semiconductors]] are produced from [[trimethylgallium]], [[trimethylindium]], [[trimethylaluminium]], and [[trimethylantimony]]. These volatile compounds are decomposed along with [[ammonia]], [[arsine]], [[phosphine]] and related hydrides on a heated substrate via [[metalorganic vapor phase epitaxy]] (MOVPE) process in the production of [[light-emitting diode]]s (LEDs). == Organometallic reactions == Organometallic compounds undergo several important reactions: * [[associative substitution|associative]] and [[dissociative substitution]] * [[oxidative addition]] and [[reductive elimination]] * [[transmetalation]] * [[migratory insertion]] * [[beta-hydride elimination|β-hydride elimination]] * [[electron transfer]] * [[carbon-hydrogen bond activation]] * [[carbometalation]] * [[hydrometalation]] * [[cyclometalation]] * [[nucleophilic abstraction]] The synthesis of many organic molecules are facilitated by organometallic complexes. [[Sigma-bond metathesis]] is a synthetic method for forming new carbon-carbon [[sigma bond]]s. Sigma-bond metathesis is typically used with early transition-metal complexes that are in their highest oxidation state.<ref>{{cite journal |last1=Waterman |first1=Rory |title=σ-Bond Metathesis: A 30-Year Retrospective |journal=Organometallics |date=23 December 2013 |volume=32 |issue=24 |pages=7249–7263 |doi=10.1021/om400760k }}</ref> Using transition-metals that are in their highest oxidation state prevents other reactions from occurring, such as [[oxidative addition]]. In addition to sigma-bond metathesis, [[olefin metathesis]] is used to synthesize various carbon-carbon [[pi bond]]s. Neither sigma-bond metathesis or olefin metathesis change the oxidation state of the metal.<ref>{{cite web |title=Olefin Metathesis |url=http://www.ilpi.com/organomet/olmetathesis.html |website=The Organometallic HyperTextBook }}</ref><ref>{{cite web |title=Sigma Bond Metathesis |url=http://www.ilpi.com/organomet/sigmabond.html |website=Organometallic HyperTextBook }}</ref> Many other methods are used to form new carbon-carbon bonds, including [[Beta-Hydride elimination|beta-hydride elimination]] and [[insertion reaction]]s. == Catalysis == Organometallic complexes are commonly used in catalysis. Major industrial processes include [[hydrogenation]], [[hydrosilylation]], [[hydrocyanation]], [[olefin metathesis]], [[alkene polymerization]], [[Shell higher olefin process|alkene oligomerization]], [[hydrocarboxylation]], [[methanol carbonylation]], and [[hydroformylation]].{{sfn|Leeuwen|2005|p={{pn|date=October 2021}}}} Organometallic intermediates are also invoked in many [[heterogeneous catalysis]] processes, analogous to those listed above. Additionally, organometallic intermediates are assumed for [[Fischer–Tropsch process]]. Organometallic complexes are commonly used in small-scale fine chemical synthesis as well, especially in [[cross-coupling reaction]]s<ref>{{cite journal |last1=Jana |first1=Ranjan |last2=Pathak |first2=Tejas P. |last3=Sigman |first3=Matthew S. |title=Advances in Transition Metal (Pd,Ni,Fe)-Catalyzed Cross-Coupling Reactions Using Alkyl-organometallics as Reaction Partners |journal=Chemical Reviews |date=9 March 2011 |volume=111 |issue=3 |pages=1417–1492 |doi=10.1021/cr100327p |pmid=21319862 |pmc=3075866 }}</ref> that form carbon-carbon bonds, e.g. [[Suzuki-Miyaura coupling]],<ref>{{cite journal |last1=Maluenda |first1=Irene |last2=Navarro |first2=Oscar |title=Recent Developments in the Suzuki-Miyaura Reaction: 2010–2014 |journal=Molecules |date=24 April 2015 |volume=20 |issue=5 |pages=7528–7557 |doi=10.3390/molecules20057528 |pmid=25919276 |pmc=6272665 |doi-access=free }}</ref> [[Buchwald-Hartwig amination]] for producing aryl amines from aryl halides,<ref>{{cite journal |last1=Magano |first1=Javier |last2=Dunetz |first2=Joshua R. |title=Large-Scale Applications of Transition Metal-Catalyzed Couplings for the Synthesis of Pharmaceuticals |journal=Chemical Reviews |date=9 March 2011 |volume=111 |issue=3 |pages=2177–2250 |doi=10.1021/cr100346g |pmid=21391570 }}</ref> and [[Sonogashira coupling]], etc. == Environmental concerns == [[File:Roxarsone.png|thumb|right|120px|[[Roxarsone]] is an organoarsenic compound used as an animal feed.]] Natural and contaminant organometallic compounds are found in the environment. Some that are remnants of human use, such as organolead and organomercury compounds, are toxicity hazards. [[Tetraethyllead]] was prepared for use as a [[gasoline]] additive but has fallen into disuse because of lead's toxicity. Its replacements are other organometallic compounds, such as [[ferrocene]] and [[methylcyclopentadienyl manganese tricarbonyl]] (MMT).<ref name="Seyferth">{{cite journal |author= Seyferth, D. |title= The Rise and Fall of Tetraethyllead. 2 |journal= [[Organometallics]] |year= 2003 |volume= 22 |pages= 5154–5178 |doi= 10.1021/om030621b |issue= 25|doi-access= free }}</ref> The [[organoarsenic compound]] roxarsone is a controversial animal feed additive. In 2006, approximately one million kilograms of it were produced in the U.S alone.<ref>{{cite journal |last1=Hileman |first1=Bette |title=Arsenic In Chicken Production |journal=Chemical & Engineering News |date=9 April 2007 |volume=85 |issue=15 |pages=34–35 |doi=10.1021/cen-v085n015.p034 |url=https://cen.acs.org/articles/85/i15/Arsenic-Chicken-Production.html }}</ref> [[Organotin compounds]] were once widely used in [[anti-fouling paint]]s but have since been banned due to environmental concerns.<ref>{{cite journal |last1=Lagerström |first1=Maria |last2=Strand |first2=Jakob |last3=Eklund |first3=Britta |last4=Ytreberg |first4=Erik |title=Total tin and organotin speciation in historic layers of antifouling paint on leisure boat hulls |journal=Environmental Pollution |date=January 2017 |volume=220 |issue=Pt B |pages=1333–1341 |doi=10.1016/j.envpol.2016.11.001 |pmid=27836476 |doi-access=free }}</ref> == See also == * [[Bioorganometallic chemistry]] * [[Metal carbon dioxide complex]] == References == {{reflist}} ==Sources== * {{cite book |last1=Clayden |first1=Jonathan |last2=Greeves |first2=Nick |last3=Warren |first3=Stuart |title=Organic Chemistry |date=2012 |publisher=OUP Oxford |isbn=978-0-19-927029-3 }} * {{cite book |last1=Crabtree |first1=Robert H. |title=The Organometallic Chemistry of the Transition Metals |date=2009 |publisher=John Wiley & Sons |isbn=978-0-470-25762-3 }} * {{cite book |last1=Elschenbroich |first1=Christoph |title=Organometallics |date=2016 |publisher=John Wiley & Sons |isbn=978-3-527-80514-3 }} * {{cite book |last1=Gupta |first1=B. D |last2=Elias |first2=A J |title=Basic Organometallic Chemistry: Concepts, Syntheses, and Applications of Transition Metals |date=2013 |publisher=Universities Press |location=Hyderabad |isbn=978-81-7371-709-3 |oclc=903314566 }} * {{cite book |last1=Jenkins |first1=Paul R. |title=Organometallic Reagents in Synthesis |date=1992 |publisher=Oxford University Press |isbn=978-0-19-855666-4 |url=https://archive.org/details/organometallicre0000jenk }} * {{cite book |last1=Leeuwen |first1=Piet W. N. M. van |title=Homogeneous Catalysis: Understanding the Art |date=2005 |publisher=Springer Science & Business Media |isbn=978-1-4020-3176-2 }} * {{cite book |last1=Lippard |first1=Stephen J. |last2=Berg |first2=Jeremy Mark |title=Principles of Bioinorganic Chemistry |date=1994 |publisher=University Science Books |isbn=978-0-935702-73-6 }} * {{cite book |last1=Pearson |first1=Anthony J |title=Metallo-organic chemistry |date=1985 |publisher=Wiley |oclc=1200566627 |url=https://archive.org/details/metalloorganicch0000pear }} * {{cite book |last1=Shriver |first1=Duward |last2=Weller |first2=Mark |last3=Overton |first3=Tina |last4=Armstrong |first4=Fraser |last5=Rourke |first5=Jonathan |title=Inorganic Chemistry |date=2014 |publisher=W. H. Freeman |isbn=978-1-4292-9906-0 }} == External links == {{wikiquote}} * [https://web.archive.org/web/20060625174426/http://ocw.mit.edu/OcwWeb/Chemistry/5-44Fall-2004/CourseHome/index.htm MIT OpenCourseWare: Organometallic Chemistry] * [http://www.ilpi.com/organomet/ Rob Toreki's Organometallic HyperTextbook] * [http://www.organometallics.net/ web listing of US chemists who specialize in organometallic chemistry] {{Webarchive|url=https://web.archive.org/web/20100811013943/http://www.organometallics.net/ |date=11 August 2010 }}. {{Organometallics}} {{BranchesofChemistry}} {{ChemicalBondsToCarbon}} {{Authority control}} {{DEFAULTSORT:Organometallic Chemistry}} [[Category:Organometallic chemistry| ]] </textarea><div class="templatesUsed"><div class="mw-templatesUsedExplanation"><p><span id="templatesused">Pages transcluded onto the current version of this page<span class="posteditwindowhelplinks"> (<a href="/wiki/Help:Transclusion" title="Help:Transclusion">help</a>)</span>:</span> 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title="Template:Reflist">view source</a>) (protected)</li><li><a href="/wiki/Template:Reflist/styles.css" title="Template:Reflist/styles.css">Template:Reflist/styles.css</a> (<a href="/w/index.php?title=Template:Reflist/styles.css&action=edit" title="Template:Reflist/styles.css">view source</a>) (protected)</li><li><a href="/wiki/Template:SDcat" title="Template:SDcat">Template:SDcat</a> (<a href="/w/index.php?title=Template:SDcat&action=edit" title="Template:SDcat">view source</a>) (protected)</li><li><a href="/wiki/Template:Sfn" title="Template:Sfn">Template:Sfn</a> (<a href="/w/index.php?title=Template:Sfn&action=edit" title="Template:Sfn">view source</a>) (template editor protected)</li><li><a href="/wiki/Template:Short_description" title="Template:Short description">Template:Short description</a> (<a href="/w/index.php?title=Template:Short_description&action=edit" title="Template:Short description">view source</a>) (protected)</li><li><a href="/wiki/Template:Short_description/lowercasecheck" title="Template:Short description/lowercasecheck">Template:Short description/lowercasecheck</a> (<a href="/w/index.php?title=Template:Short_description/lowercasecheck&action=edit" title="Template:Short description/lowercasecheck">view source</a>) (protected)</li><li><a href="/wiki/Template:Side_box" title="Template:Side box">Template:Side box</a> (<a href="/w/index.php?title=Template:Side_box&action=edit" title="Template:Side box">view source</a>) (template editor protected)</li><li><a href="/wiki/Template:Sister_project" title="Template:Sister project">Template:Sister project</a> (<a href="/w/index.php?title=Template:Sister_project&action=edit" title="Template:Sister project">view source</a>) (template editor protected)</li><li><a href="/wiki/Template:Sister_project/styles.css" title="Template:Sister project/styles.css">Template:Sister project/styles.css</a> (<a 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href="/w/index.php?title=Template:Use_dmy_dates&action=edit" title="Template:Use dmy dates">view source</a>) (template editor protected)</li><li><a href="/wiki/Template:Webarchive" title="Template:Webarchive">Template:Webarchive</a> (<a href="/w/index.php?title=Template:Webarchive&action=edit" title="Template:Webarchive">view source</a>) (template editor protected)</li><li><a href="/wiki/Template:Wikiquote" title="Template:Wikiquote">Template:Wikiquote</a> (<a href="/w/index.php?title=Template:Wikiquote&action=edit" title="Template:Wikiquote">view source</a>) (template editor protected)</li><li><a href="/wiki/Template:Yesno" title="Template:Yesno">Template:Yesno</a> (<a href="/w/index.php?title=Template:Yesno&action=edit" title="Template:Yesno">view source</a>) (protected)</li><li><a href="/wiki/Template:Yesno-no" title="Template:Yesno-no">Template:Yesno-no</a> (<a href="/w/index.php?title=Template:Yesno-no&action=edit" title="Template:Yesno-no">view source</a>) (template editor 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href="/wiki/Module:Catalog_lookup_link" title="Module:Catalog lookup link">Module:Catalog lookup link</a> (<a href="/w/index.php?title=Module:Catalog_lookup_link&action=edit" title="Module:Catalog lookup link">view source</a>) (template editor protected)</li><li><a href="/wiki/Module:Category_handler" title="Module:Category handler">Module:Category handler</a> (<a href="/w/index.php?title=Module:Category_handler&action=edit" title="Module:Category handler">view source</a>) (protected)</li><li><a href="/wiki/Module:Category_handler/blacklist" title="Module:Category handler/blacklist">Module:Category handler/blacklist</a> (<a href="/w/index.php?title=Module:Category_handler/blacklist&action=edit" title="Module:Category handler/blacklist">view source</a>) (protected)</li><li><a href="/wiki/Module:Category_handler/config" title="Module:Category handler/config">Module:Category handler/config</a> (<a href="/w/index.php?title=Module:Category_handler/config&action=edit" title="Module:Category 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title="Module:Citation/CS1/Identifiers">Module:Citation/CS1/Identifiers</a> (<a href="/w/index.php?title=Module:Citation/CS1/Identifiers&action=edit" title="Module:Citation/CS1/Identifiers">view source</a>) (protected)</li><li><a href="/wiki/Module:Citation/CS1/Utilities" title="Module:Citation/CS1/Utilities">Module:Citation/CS1/Utilities</a> (<a href="/w/index.php?title=Module:Citation/CS1/Utilities&action=edit" title="Module:Citation/CS1/Utilities">view source</a>) (protected)</li><li><a href="/wiki/Module:Citation/CS1/Whitelist" title="Module:Citation/CS1/Whitelist">Module:Citation/CS1/Whitelist</a> (<a href="/w/index.php?title=Module:Citation/CS1/Whitelist&action=edit" title="Module:Citation/CS1/Whitelist">view source</a>) (protected)</li><li><a href="/wiki/Module:Citation/CS1/styles.css" title="Module:Citation/CS1/styles.css">Module:Citation/CS1/styles.css</a> (<a href="/w/index.php?title=Module:Citation/CS1/styles.css&action=edit" title="Module:Citation/CS1/styles.css">view 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