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Heck Coupling
The Heck reaction
Heck reaction
(also called the Mizoroki-Heck reaction)[1] is the chemical reaction of 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.[2][3] It is named after Tsutomu Mizoroki and Richard F. Heck. Heck was awarded the 2010 Nobel Prize in Chemistry, which he shared with Ei-ichi Negishi
Ei-ichi Negishi
and Akira Suzuki, for the discovery and development of this reaction. This reaction was the first example of a carbon-carbon bond-forming reaction that followed a Pd(0)/Pd(II) catalytic cycle, the same catalytic cycle that is seen in other Pd(0)-catalyzed cross-coupling reactions
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Richard F. Heck
Richard Frederick Heck (August 15, 1931 – October 10, 2015) was an American chemist noted for the discovery and development of the Heck reaction, which uses palladium to catalyze organic chemical reactions that couple aryl halides with alkenes. The analgesic naproxen is an example of a compound that is prepared industrially using the Heck reaction. For his work in palladium-catalyzed coupling reactions and organic synthesis, Heck was awarded the 2010 Nobel Prize
Nobel Prize
in Chemistry, shared with the Japanese chemists Ei-ichi Negishi
Ei-ichi Negishi
and Akira Suzuki.[3]Contents1 Early life and education 2 Career2.1 Palladium-catalyzed coupling reactions3 Later life and death 4 Honors 5 References 6 Further reading 7 External linksEarly life and education[edit] Heck was born in Springfield, Massachusetts
Springfield, Massachusetts
in 1931.[4] He earned his Ph.D
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Palladium Acetate
Palladium(II) acetate
Palladium(II) acetate
is a chemical compound of palladium described by the formula [Pd(O2CCH3)2]n, abbreviated [Pd(OAc)2]n. It is more reactive than the analogous platinum compound. Depending on the value of n, the compound is soluble in many organic solvents and is commonly used as a catalyst for organic reactions.Contents1 Structure 2 Preparation 3 Catalysis 4 Precursor to other Pd compounds 5 See also 6 ReferencesStructure[edit] With a 1:2 stoichiometric ratio of palladium atoms and acetate ligands, the compound exists as molecular and polymeric forms. Pd achieves approximate square planar coordination in both forms. As prepared by Wilkinson and coworkers in 1965 and later characterized by Skapski and Smart in 1970 by single crystal X-ray diffraction, palladium(II) acetate is a red-brown solid that crystallizes as monoclinic plates
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BINAP
BINAP
BINAP
(2,2'-bis(diphenylphosphino)-1,1'-binaphthyl) is an organophosphorus compound. This chiral ligand is widely used in asymmetric synthesis. It consists of a pair of 2-diphenylphosphinonaphthyl groups linked at the 1 and 1´ positions. This C2-symmetric framework lacks a stereogenic atom, but has axial chirality due to restricted rotation (atropisomerism). The barrier to racemization is high due to steric hindrance, which limits rotation about the bond linking the naphthyl rings
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Triethylamine
Triethylamine
Triethylamine
is the chemical compound with the formula N(CH2CH3)3, commonly abbreviated Et3N. It is also abbreviated TEA, yet this abbreviation must be used carefully to avoid confusion with triethanolamine or tetraethylammonium, for which TEA is also a common abbreviation. It is a colourless volatile liquid with a strong fishy odor reminiscent of ammonia and is also the smell of the hawthorn plant.[7] Like diisopropylethylamine (Hünig’s base), triethylamine is commonly encountered in organic synthesis.Contents1 Synthesis and properties 2 Applications2.1 Niche uses3 References 4 External linksSynthesis and properties[edit] Triethylamine
Triethylamine
is prepared by the alkylation of ammonia with ethanol:[8]NH3 + 3 C2H5OH → N(C2H5)3 + 3 H2OThe pKa of protonated triethylamine is 10.75,[3] and it can be used to prepare buffer solutions for that pH
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Potassium Carbonate
Potassium
Potassium
carbonate (K2CO3) is a white salt, soluble in water (insoluble in ethanol)[2] which forms a strongly alkaline solution. It can be made as the product of potassium hydroxide's absorbent reaction with carbon dioxide. It is deliquescent, often appearing a damp or wet solid. Potassium
Potassium
carbonate is used in the production of soap and glass.Contents1 History 2 Production 3 Applications 4 References 5 Bibliography 6 External linksHistory[edit] Potassium
Potassium
carbonate is the primary component of potash and the more refined pearl ash or salts of tartar. Historically, pearl ash was created by baking potash in a kiln to remove impurities. The fine, white powder remaining was the pearl ash
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Sodium Acetate
Sodium
Sodium
acetate, CH3COONa, also abbreviated NaOAc,[8] is the sodium salt of acetic acid. This colorless deliquescent salt has a wide range of uses.Contents1 Applications1.1 Industrial 1.2 Concrete
Concrete
longevity 1.3 Food 1.4 Buffer solution 1.5 Heating pad2 Preparation 3 Reactions 4 References 5 External linksApplications[edit] Industrial[edit] Sodium
Sodium
acetate is used in the textile industry to neutralize sulfuric acid waste streams and also as a photoresist while using aniline dyes. It is also a pickling agent in chrome tanning and helps to impede vulcanization of chloroprene in synthetic rubber production
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Iodobenzene
Iodobenzene
Iodobenzene
is an organoiodine compound consisting of a benzene ring substituted with one iodine atom. It is useful as a synthetic intermediate in organic chemistry. It is a volatile colorless liquid, although aged samples appear yellowish.Contents1 Preparation 2 Reactions 3 See also 4 References 5 Further readingPreparation[edit] Iodobenzene
Iodobenzene
is commercially available, but it can be prepared in the laboratory from aniline via the Sandmeyer reaction. In the first step, the amine functional group is diazotized with hydrochloric acid and sodium nitrite. Potassium iodide
Potassium iodide
is added to the resultant phenyldiazonium chloride, causing nitrogen gas to evolve
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Styrene
Styrene, also known as ethenylbenzene, vinylbenzene, and phenylethene, is an organic compound with the chemical formula C6H5CH=CH2. This derivative of benzene is a colorless oily liquid that evaporates easily and has a sweet smell, although high concentrations have a less pleasant odor. Styrene
Styrene
is the precursor to polystyrene and several copolymers
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Stilbene
Stilbene may refer to one of the two stereoisomers of 1,2-diphenylethene: (E)-Stilbene
(E)-Stilbene
(trans isomer) (Z)-Stilbene
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Methanol
Methanol, also known as methyl alcohol among others, is a chemical with the formula CH3OH (often abbreviated MeOH). Methanol
Methanol
acquired the name wood alcohol because it was once produced chiefly as a byproduct of the destructive distillation of wood. Today, industrial methanol is produced in a catalytic process directly from carbon monoxide, carbon dioxide, and hydrogen. Methanol
Methanol
is the simplest alcohol, being only a methyl group linked to a hydroxyl group. It is a light, volatile, colorless, flammable liquid with a distinctive odor very similar to that of ethanol (drinking alcohol).[11] However, unlike ethanol, methanol is highly toxic and unfit for consumption. At room temperature, it is a polar liquid. It is used as an antifreeze, solvent, fuel, and as a denaturant for ethanol
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Autoclave
An autoclave is a pressure chamber used to carry out industrial processes requiring elevated temperature and pressure different from ambient air pressure. Autoclaves are used in medical applications to perform sterilization and in the chemical industry to cure coatings and vulcanize rubber and for hydrothermal synthesis
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Potassium Acetate
Potassium
Potassium
acetate (KCH3COO) is the potassium salt of acetic acid.Contents1 Preparation 2 Applications2.1 Deicing 2.2 Fire extinguishing 2.3 Food additive 2.4 Medicine and biochemistry 2.5 Death penalty 2.6 Industry3 Historical 4 References 5 External linksPreparation[edit] It can be prepared by treating a potassium-containing base such as potassium hydroxide or potassium carbonate with acetic acid:CH3COOH + KOH → CH3COOK + H2OThis sort of reaction is known as an acid-base neutralization reaction. The sesquihydrate in water solution (CH3COOK·1½H2O) begins to form semihydrate at 41.3 °C.[2] Applications[edit] Deicing[edit] Potassium
Potassium
acetate can be used as a deicer to remove ice and prevent its formation. It is a supstitute for chloride salts such as calcium chloride or magnesium chloride in deicing applications
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Catalytic Cycle
In chemistry, a catalytic cycle is a multistep reaction mechanism that involves a catalyst.[1] The catalytic cycle is the main method for describing the role of catalysts in biochemistry, organometallic chemistry, bioinorganic chemistry, materials science, etc. Often such cycles show the conversion of a precatalyst to the catalyst. Since catalysts are regenerated, catalytic cycles are usually written as a sequence of chemical reactions in the form of a loop. In such loops, the initial step entails binding of one or more reactants by the catalyst, and the final step is the release of the product and regeneration of the catalyst. Articles on the Monsanto process, the Wacker process, and the Heck reaction show catalytic cycles. Catalytic cycle
Catalytic cycle
for conversion of A and B into C.A catalytic cycle is not necessarily a full reaction mechanism
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Triphenylphosphine
Triphenylphosphine
Triphenylphosphine
(IUPAC name: triphenylphosphane) is a common organophosphorus compound with the formula P(C6H5)3 - often abbreviated to PPh3 or Ph3P. It is widely used in the synthesis of organic and organometallic compounds. PPh3 exists as relatively air stable, colorless crystals at room temperature
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In Situ
In situ
In situ
(/ɪn ˈsɪtjuː/ or /ɪn ˈsaɪtʃuː/ or /ɪn ˈsiːtuː/; often not italicized in English[1][2][3]) is a Latin
Latin
phrase that translates literally to "on site"[4] or "in position".[5] It means "locally", "on site", "on the p
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