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Coupling Reaction
A coupling reaction in organic chemistry is a general term for a variety of reactions where two fragments are joined together with the aid of a metal catalyst. In one important reaction type, a main group organometallic compound of the type R-M (R = organic fragment, M = main group center) reacts with an organic halide of the type R'-X with formation of a new carbon-carbon bond in the product R-R'. The most common type of coupling reaction is the cross coupling reaction. Richard F. Heck, Ei-ichi Negishi, and Akira Suzuki were awarded the 2010 Nobel Prize in Chemistry for developing palladium-catalyzed cross coupling reactions. Broadly speaking, two types of coupling reactions are recognized: *Heterocouplings combine two different partners, such as in the Heck reaction of an alkene (RC=CH) and an alkyl halide (R'-X) to give a substituted alkene, or the Corey–House synthesis of an alkane by the reaction of a lithium diorganylcuprate (R2CuLi) with an organyl (pseudo)halide (R ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Organic Chemistry
Organic chemistry is a subdiscipline within chemistry involving the scientific study of the structure, properties, and reactions of organic compounds and organic materials, i.e., matter in its various forms that contain carbon atoms.Clayden, J.; Greeves, N. and Warren, S. (2012) ''Organic Chemistry''. Oxford University Press. pp. 1–15. . Study of structure determines their structural formula. Study of properties includes physical and chemical properties, and evaluation of chemical reactivity to understand their behavior. The study of organic reactions includes the chemical synthesis of natural products, drugs, and polymers, and study of individual organic molecules in the laboratory and via theoretical ( in silico) study. The range of chemicals studied in organic chemistry includes hydrocarbons (compounds containing only carbon and hydrogen) as well as compounds based on carbon, but also containing other elements, especially oxygen, nitrogen, sulfur, phosphorus (i ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Cuprate
Cuprate loosely refers to a material that can be viewed as containing anionic copper complexes. Examples include tetrachloridocuprate ( uCl4sup>2−), the superconductor YBa2Cu3O7, and the organocuprates (e.g., dimethylcuprate u(CH3)2sup>−). The term cuprates derives from the Latin word for copper, ''cuprum''. The term is mainly used in three contexts: oxide materials, anionic coordination complexes, and anionic organocopper compounds. Oxides One of the simplest oxide-based cuprates is the copper(III) oxide KCuO2, also known as "potassium cuprate(III)". This species can be viewed as the K+ salt of the polyanion []''n''. As such the material is classified as a cuprate. This dark blue diamagnetic solid is produced by heating potassium peroxide and copper(II) oxide in an atmosphere of oxygen: :K2O2 + 2 CuO → 2 KCuO2 Sodium cuprate(III) NaCuO2 and potassium cuprate(III) KCuO2 can also be produced by using hypochlorites or hypobromites to oxidize copper hydroxide under ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Grignard Reaction
The Grignard reaction () is an organometallic chemical reaction in which alkyl, allyl, vinyl, or aryl-magnesium halides (Grignard reagent) is added to a carbonyl group in an aldehyde or ketone. This reaction is important for the formation of carbon–carbon bonds. The reaction of an organic halide with magnesium is ''not'' a Grignard reaction, but provides a Grignard reagent. : Grignard reactions and reagents were discovered by and are named after the French chemist François Auguste Victor Grignard ( University of Nancy, France), who published it in 1900 and was awarded the 1912 Nobel Prize in Chemistry for this work. Reaction mechanism Because carbon is more electronegative than magnesium, the carbon attached to magnesium functions as a nucleophile and attacks the electrophilic carbon atom that is present within the polar bond of a carbonyl group. The addition of the Grignard reagent to the carbonyl typically proceeds through a six-membered ring transition state. Based ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Heck Reaction Scheme
Heck may refer to: * HECK (band), a British rock band * Heck (surname) * Heck, Dumfries and Galloway, Scotland * Heck, North Yorkshire, England * Heck cattle * Heck horse * Heck reaction, a chemical reaction that forms a substituted alkene * Parnall Heck, a 1930s British four-seat cabin monoplane * NOAAS ''Heck'' (S 591), originally USC&GS ''Heck'', a survey ship * A minced oath for "hell" Hecke may refer to: * Hecke algebra (other) * Hecke character In number theory, a Hecke character is a generalisation of a Dirichlet character, introduced by Erich Hecke to construct a class of ''L''-functions larger than Dirichlet ''L''-functions, and a natural setting for the Dedekind zeta-functions an ... * Hecke operator * Hecke (surname) {{disambiguation, geo ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Pinacol Coupling Reaction
A pinacol coupling reaction is an organic reaction in which a carbon–carbon bond is formed between the carbonyl groups of an aldehyde or a ketone in presence of an electron donor in a free radical process. The reaction product is a vicinal diol. The reaction is named after pinacol (also known as 2,3-dimethyl-2,3-butanediol or tetramethylethylene glycol), which is the product of this reaction when done with acetone as reagent. The reaction is usually a homocoupling but intramolecular cross-coupling reactions are also possible. Pinacol was discovered by Wilhelm Rudolph Fittig in 1859. Reaction mechanism The first step in the reaction mechanism is a one-electron reduction of the carbonyl group by a reducing agent —such as magnesium— to a ketyl radical anion species. Two ketyl groups react in a coupling reaction yielding a vicinal diol with both hydroxyl groups deprotonated. Addition of water or another proton donor gives the diol. With magnesium as an electron donor, the initia ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Wurtz Reaction
In organic chemistry, the Wurtz reaction, named after Charles Adolphe Wurtz, is a coupling reaction whereby two alkyl halides are treated with sodium metal to form a higher alkane. : 2 R−X + 2 Na → R−R + 2 NaX The reaction is of little value except for intramolecular versions. A related reaction, which combines alkyl halides with aryl halides is called the Wurtz–Fittig reaction. Mechanism The reaction proceeds by an initial metal–halogen exchange, which involves this idealized stoichiometry: : R−X + 2 M → RM + MX This step involves the intermediacy of radical species R·. This step resembles the formation of a Grignard reagent. These RM intermediates have been isolated in several cases. The organometallic intermediate next reacts with the alkyl halide forming a new carbon–carbon covalent bond. : RM + RX → R−R + MX The process resembles an SN2 reaction, but the process is probably complex, which may explain the inefficiency of the reaction. Exam ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Ullmann Reaction
The Ullmann reaction or Ullmann coupling is a coupling reaction between aryl halides. Traditionally this reaction is effected by copper, but palladium and nickel are also effective catalysts. The reaction is named after Fritz Ullmann. Mechanism The mechanism of the Ullmann reaction is extensively studied. Complications arise because the reactions are often heterogeneous. With copper as the halide acceptor, organocopper intermediates are invoked. Scope A typical example of classic Ullmann biaryl coupling is the conversion of ''ortho''-chloronitrobenzene into 2,2'-dinitrobiphenyl with a copper - bronze alloy. : : The traditional version of the Ullmann reaction requires harsh reaction conditions, and the reaction has a reputation for erratic yields. Because of these problems many improvements and alternative procedures have been introduced. The classical Ullmann reaction is limited to electron deficient aryl halides and requires harsh reaction conditions. Modern variants of ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Acetylide
In organometallic chemistry, acetylide refers to chemical compounds with the chemical formulas and , where M is a metal. The term is used loosely and can refer to substituted acetylides having the general structure (where R is an organic side chain). Acetylides are reagents in organic synthesis. The calcium acetylide commonly called calcium carbide is a major compound of commerce. Structure and bonding Alkali metal and alkaline earth metal acetylides of the general formula MC≡CM are salt-like Zintl phase compounds, containing ions. Evidence for this ionic character can be seen in the ready hydrolysis of these compounds to form acetylene and metal oxides, there is also some evidence for the solubility of ions in liquid ammonia. The ion has a closed shell ground state of 1Σ, making it isoelectronic to a neutral molecule N2, which may afford it some stability. Analogous acetylides prepared from other metals, particularly transition metals, show covalent character and a ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Glaser Coupling
The Glaser coupling is a type of coupling reaction. It is by far the oldest acetylenic coupling and is based on cuprous salts like copper(I) chloride or copper(I) bromide and an additional oxidant like oxygen. The base in its original scope is ammonia. The solvent is water or an alcohol. The reaction was first reported by in 1869. He suggested the following process for his way to diphenylbutadiyne: :CuCl + PhC2H + NH3 → PhC2Cu + NH4Cl :2PhC2Cu + O → PhC2C2Ph + Cu2O Modifications Eglinton reaction In the related Eglinton reaction two terminal alkynes are coupled by a copper(II) salt such as cupric acetate. :2R-\!\!-H -> ce\ce] R-\!\!-\!\!-R The oxidative coupling of alkynes has been used to synthesize a number of fungal antibiotics. The stoichiometry is represented by this highly simplified scheme: : Such reactions proceed via metal-alkyne complex, copper(I)-alkyne complexes. This methodology was used in the synthesis of cyclooctadecanonaene. Another example is the synth ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
