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    Organometallic Compunds: D. JIM LIVINGSTON, Asst - Prof in Chemistry, ST - John's College, Palai

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    Jim Livingston
    Organometallic compounds are chemical compounds containing at least one chemical bond between a carbon atom of an organic molecule and a metal, including alkaline, alkaline earth, and transition metals, and sometimes broadened to include metalloids. They are used both as a catalyst and reagent in the synthesis of organic compounds.

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    Organometallic Compunds: D. JIM LIVINGSTON, Asst - Prof in Chemistry, ST - John's College, Palai

    Uploaded by

    Jim Livingston
    457 views23 pages
    Organometallic compounds are chemical compounds containing at least one chemical bond between a carbon atom of an organic molecule and a metal, including alkaline, alkaline earth, and transition metals, and sometimes broadened to include metalloids. They are used both as a catalyst and reagent in the synthesis of organic compounds.

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    Organometallic Compounds -Intro

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    Organometallic compounds are chemical compounds containing at least one chemical bond between a carbon atom of an organic molecule and a metal, including alkaline, alkaline earth, and transition metals, and sometimes broadened to include metalloids. They are used both as a catalyst and reagent in the synthesis of organic compounds.

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    © All Rights Reserved
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    Download as ppt, pdf, or txt
    457 views23 pages

    Organometallic Compunds: D. JIM LIVINGSTON, Asst - Prof in Chemistry, ST - John's College, Palai

    Uploaded by

    Jim Livingston
    Organometallic compounds are chemical compounds containing at least one chemical bond between a carbon atom of an organic molecule and a metal, including alkaline, alkaline earth, and transition metals, and sometimes broadened to include metalloids. They are used both as a catalyst and reagent in the synthesis of organic compounds.

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    of 23

    Organometallic

    Compunds

    12/5/2018 D. JIM LIVINGSTON, Asst.Prof in Chemistry,


    St.John’s College, Palai.
    What is organometallic chemistry?

    Compounds having at least one bond between carbon of


    an organic functional group and metal are known as
    organometallic compounds
    In many compounds, both σ- and π-bonding exist
    between the metal

    (AlMe3)2

    12/5/2018 D. JIM LIVINGSTON, AP (Chem)


    A brief history of organometallic chemistry

    Organometallic Vitamin B12


    Chemistry has
    really been around
    for millions of
    years

    12/5/2018 D. JIM LIVINGSTON, AP (Chem)


    Naturally occurring Cobalimins contain Co—C
    bonds

    12/5/2018 D. JIM LIVINGSTON, AP (Chem)


    Tetramethyldiarsine

     1st organometalic compound - Louis Claude Cadet de Gassicourt


    French chemist
     organoarsenic compound – aka Cacodyl or dicacodyl
     Greek kakodes (evil-smelling)
     It is a poisonous oily liquid with an extremely unpleasant garlicky odor.
     “when one is exposed to the smell of these compounds the tongue becomes
    covered with a black coating even when no further evil effects are
    noticeable". Bunsen's words

    12/5/2018 D. JIM LIVINGSTON, AP (Chem)


    Zeise's salt

     William Christopher Zeise


     potassium trichloro(ethene)platinate(II) -K[PtCl3(C2H4)]·H2O.
     1st example of a transition metal alkene complex
     yellow, coordination complex contains an η2-ethylene ligand with a square
    planar geometry..

    12/5/2018 D. JIM LIVINGSTON, AP (Chem)


    Diethylzinc or DEZ

     a highly pyrophoric and reactive organozinc compound


     colourless liquid used in organic synthesis as a source of the ethyl carbanion
    in addition reactions to carbonyl groups.
     high reactivity toward air, it was used in small quantities as a hypergolic or "self
    igniting" liquid rocket fuel.

    12/5/2018 D. JIM LIVINGSTON, AP (Chem)


    Nickel tetracarbonyl
     This pale-yellow liquid an intermediate in the Mond process for the
    purification of nickel and a reagent in organometallic chemistry.
     Nickel carbonyl is one of the most toxic substances encountered in
    industrial processes

    12/5/2018 D. JIM LIVINGSTON, AP (Chem)


    Grignard reagent,

     Victor Grignard 1912 Nobel Prize


     organic derivatives of magnesium (Mg)
     RMgX
     R is a hydrocarbon radical: CH3, C2H5, C6H5, etc.; and X is a halogen atom,
    usually chlorine, bromine, or iodine.

    12/5/2018 D. JIM LIVINGSTON, AP (Chem)


    Applications
     in the industrial production of Tamoxifen currently used for the treatment of
    positive breast cancer in women
     sold under the brand name Nolvadex
     Tamoxifen is used to treat infertility in women with anovulatory
    disorders

    12/5/2018 D. JIM LIVINGSTON, AP (Chem)


    Gilman Reagent
     American chemist Henry Gilman – 1930
     organocopper compounds
     lithium dimethylcopper reagentsimilar to
    Grignard reagents.
     used for carbon-carbon bond formation in
    organic synthesis

    12/5/2018 D. JIM LIVINGSTON, AP (Chem)


    Ferrocene
     Ferrocene (metallocene) a type of organometallic chemical compound
    consisting of two cyclopentadienyl rings bound on opposite
    sides of a central metal atom.
     Discovered in 1951.
     known as sandwich compounds.

    12/5/2018 D. JIM LIVINGSTON, AP (Chem)


     antiknock agents used in the fuel for petrol engines
    they are safer than tetraethyllead, previously used
     Ferroquine (7-chloro-N-(2-
    ((dimethylamino)methyl)ferrocenyl)quinolin-4-amine),
    an antimalarial.
     a precursor to iron nanoparticles, can be used as a
    catalyst for the production of carbon nanotubes

    12/5/2018 D. JIM LIVINGSTON, AP (Chem)


    Ziegler–Natta catalyst
    Karl Ziegler Giulio Natta

     Titanium compounds in combination, organoaluminum compounds.


     used to polymerize terminal alkenes (ethylene and alkenes with the vinyl double
    bond)
     1963 Nobel Prize

    12/5/2018 D. JIM LIVINGSTON, AP (Chem)


    Transition metal carbene
    complex
     organometallic compound featuring a divalent
    organic ligand
     Fischer -1964 (CO)5W=C(Ph)(OMe)
     Classified into two types. Fischer carbenes,
    Schrock carbenes
     These are heterogeneous catalysts used for
    alkene metathesis
     1973 - the Nobel Prize in Chemistry

    12/5/2018 D. JIM LIVINGSTON, AP (Chem)


    Alkene Metathesis
     Alkene metathesis or Olefin metathesis is an organic reaction
    that entails the redistribution of fragments of alkenes (olefins) by
    the scission and regeneration of carbon-carbon double bonds

    12/5/2018 D. JIM LIVINGSTON, AP (Chem)


    Robert Grubbs
    Alkene Metathesis Richard Schrock

     awarded the 2005 Nobel Prize in Chemistry.

    12/5/2018 D. JIM LIVINGSTON, AP (Chem)


    Palladium-catalyzed coupling
    reactions
     cross-coupling reactions that employ palladium complexes as catalysts.
     active area of research and applications in homogeneous catalysis.
     In 2010, the Nobel Prize in Chemistry was awarded to Richard F. Heck,
    Ei-ichi Negishi, Akira Suzuki

     Typical palladium catalysts used include the following compounds:

     palladium acetate, Pd(OAc)2


     tetrakis(triphenylphosphine)palladium(0), Pd(PPh3)4
     bis(triphenylphosphine)palladium(II) dichloride, PdCl2(PPh3)2
     [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) dichlorideard F.
    Heck, Ei-ichi Negishi and Akira Suzuki

    D. JIM LIVINGSTON, AP (Chem)


    12/5/2018
    Heck reaction (coupling reaction)

     Coupling reaction - two hydrocarbon


    fragments are joined together with the
    aid of a metal catalyst.

     Heck reaction - an unsaturated halide (or triflate) with an alkene in the


    presence of a base and a palladium catalyst (or palladium nanomaterial-
    based catalyst) to form a substituted alkene

    12/5/2018 D. JIM LIVINGSTON, AP (Chem)


    Suzuki coupling
     Suzuki reaction is an organic reaction, classified as
    a coupling reaction, where the coupling partners
    are a boronic acid and an organohalide
    catalyzed by a palladium(0) complex

    12/5/2018 D. JIM LIVINGSTON, AP (Chem)


    Sonogashira reaction
     a cross-coupling reaction employs a palladium
    catalyst as well as copper co-catalyst.
     Formation of carbon–carbon bond between a
    terminal alkyne and an aryl or vinyl halide

    12/5/2018 D. JIM LIVINGSTON, AP (Chem)


    Stille reaction
     The Stille reaction involves the coupling of an organotin
    compound (organostannanes) with a variety of organic
    electrophiles via palladium-catalyzed coupling reaction

    12/5/2018 D. JIM LIVINGSTON, AP (Chem)


    12/5/2018 D. JIM LIVINGSTON, AP (Chem)

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