| 词条 | Oxidative coupling |
| 释义 |
C-C CouplingsMany oxidative couplings generate new C-C bonds. Early examples involve coupling of terminal alkynes:[2] 2 RC≡CH + 2 Cu(I) → RC≡C-C≡CR + 2 Cu + 2 H+ Coupling of methaneCoupling reactions involving methane are highly sought, related to C1 chemistry because C2 derivatives are far more valuable than methane. The oxidative coupling of methane gives ethylene:[3][4] 2{{chem|CH|4}} + {{chem|O|2}} → {{chem|C|2|H|4}} + 2{{chem|H|2|O}} Aromatic couplingIn oxidative aromatic coupling the reactants are electron-rich aromatic compounds. Typical substrates are phenols and typical catalysts are copper and iron compounds and enzymes.[6] The first reported synthetic application dates back to 1868 with Julius Löwe and the synthesis of ellagic acid by heating gallic acid with arsenic acid or silver oxide.[7] Another reaction is the synthesis of 1,1'-Bi-2-naphthol from 2-naphthol by iron chloride, discovered in 1873 by Alexander Dianin [8] (S)-BINOL can be prepared directly from an asymmetric oxidative coupling of 2-naphthol with copper(II) chloride.[9] Other oxidative couplingsThe oxygen evolution reaction entails, in effect, the oxidative coupling of water molecules to give O2. References1. ^IUPAC. Compendium of Chemical Terminology, 2nd ed. (the "Gold Book"). Compiled by A. D. McNaught and A. Wilkinson. Blackwell Scientific Publications, Oxford (1997). {{doi|10.1351/goldbook}} 2. ^{{cite journal|title=Copper‐Catalyzed Aerobic Oxidative C-H Functionalizations: Trends and Mechanistic Insights|authors=Alison E. Wendlandt, Alison M. Suess, Shannon S. Stahl|journal=Angew. Chem. Int. Ed.|year=2011|volume=50|pages=11062-11087|doi=10.1002/anie.201103945}} 3. ^{{cite journal| author=Zhang, Q. |year = 2003| title = Recent Progress in Direct Partial Oxidation of Methane to Methanol | journal =J. Natural Gas Chem.| volume = 12|pages = 81–89}} 4. ^Olah, G., Molnar, A. “Hydrocarbon Chemistry” John Wiley & Sons, New York, 2003. {{ISBN|978-0-471-41782-8}}. 5. ^{{cite encyclopedia |last=Lebo |first=Stuart E. Jr. |authorlink= |author2=Gargulak, Jerry D. |author3=McNally, Timothy J. |encyclopedia=Kirk‑Othmer Encyclopedia of Chemical Technology |url= http://www.mrw.interscience.wiley.com/emrw/9780471238966/kirk/article/lignlin.a01/current/pdf |accessdate=2007-10-14 |year=2001 |publisher= John Wiley & Sons, Inc |doi=10.1002/0471238961.12090714120914.a01.pub2 |chapter=Lignin |title=Kirk-Othmer Encyclopedia of Chemical Technology |isbn=0-471-23896-1 }} 6. ^Grzybowski, M., Skonieczny, K., Butenschön, H. and Gryko, D. T. (2013), Comparison of Oxidative Aromatic Coupling and the Scholl Reaction Angew. Chem. Int. Ed., 52: 9900–9930. {{doi|10.1002/anie.201210238}} 7. ^Löwe, Zeitschrift für Chemie, 1868, 4, 603 8. ^A. P. Dianin, Zh. Russ. Fiz.-Khim. O-va. 1874 , 183 9. ^{{cite journal|last1 = Brussee|first1 = J.|last2 = Jansen|first2 = A. C. A.|year = 1983|title = A highly stereoselective synthesis of S-(−)-[1,1′-binaphthalene]-2,2′-diol|journal = Tetrahedron Letters|volume = 24|issue = 31|pages = 3261–3262|doi = 10.1016/S0040-4039(00)88151-4}} 1 : Chemical reactions |
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