• Chao LiuEmail author
Part of the Lecture Notes in Chemistry book series (LNC, volume 102)


Oxidative coupling has now been more and more applied in the description of bond formations between two nucleophiles. As the introduction of this whole book, in this chapter, the concept of oxidative coupling, the history of oxidative coupling, and the principle of oxidative coupling were generally introduced. Finally, the developments and outlook of this area were discussed.


Oxidative coupling Nucleophiles Concept Understanding 


  1. 1.
    Baba S, Negishi E (1976) A novel stereospecific alkenyl-alkenyl cross-coupling by a palladium- or nickel-catalyzed reaction of alkenylalanes with alkenyl halides. J Am Chem Soc 98:6729–6731. CrossRefGoogle Scholar
  2. 2.
    Ghose R, Hwang HT, Varma A (2014) Oxidative coupling of methane using catalysts synthesized by solution combustion method: catalyst optimization and kinetic studies. Appl Catal A 472:39–46. CrossRefGoogle Scholar
  3. 3.
    Glaser C (1869) Beiträge zur Kenntniss des Acetenylbenzols. Ber Dtsch Chem Ges 2:422–424. CrossRefGoogle Scholar
  4. 4.
    Guram AS, Rennels RA, Buchwald SL (1995) A simple catalytic method for the conversion of aryl bromides to Arylamines. Angew Chem Int Ed 34:1348–1350. CrossRefGoogle Scholar
  5. 5.
    Hatanaka Y, Hiyama T (1988) Cross-coupling of organosilanes with organic halides mediated by a palladium catalyst and tris(diethylamino)sulfonium difluorotrimethylsilicate. J Org Chem 53:918–920. CrossRefGoogle Scholar
  6. 6.
    Heck RF, Nolley JP (1972) Palladium-catalyzed vinylic hydrogen substitution reactions with aryl, benzyl, and styryl halides. J Org Chem 37:2320–2322. CrossRefGoogle Scholar
  7. 7.
    Keller G (1982) Synthesis of ethylene via oxidative coupling of methane I. Determination of active catalysts. J Catal 73:9–19. CrossRefGoogle Scholar
  8. 8.
    Li CJ (2009) Cross-dehydrogenative coupling (CDC): exploring C-C bond formations beyond functional group transformations. Acc Chem Res 42:335–344. CrossRefGoogle Scholar
  9. 9.
    Liu C, Jin L, Lei A (2010) Transition-metal-catalyzed oxidative cross-coupling reactions. Synlett 2010:2527–2536. CrossRefGoogle Scholar
  10. 10.
    Liu C, Zhang H, Shi W, Lei A (2011) Bond formations between two nucleophiles: transition metal catalyzed oxidative cross-coupling reactions. Chem Rev 111:1780–1824. CrossRefPubMedPubMedCentralGoogle Scholar
  11. 11.
    Liu C, Liu D, Lei A (2014) Recent advances of transition-metal catalyzed radical oxidative cross-couplings. Acc Chem Res 47:3459–3470. CrossRefGoogle Scholar
  12. 12.
    Liu C, Yuan J, Gao M, Tang S, Li W, Shi R, Lei A (2015) Oxidative coupling between two hydrocarbons: an update of recent C-H Functionalizations. Chem Rev 115:12138–12204. CrossRefPubMedGoogle Scholar
  13. 13.
    Meijere AD, Diederich F (2004) Metal-catalyzed cross-coupling reactions. 2nd, completely rev. and enl. Edn. Wiley-VCH, WeinheimCrossRefGoogle Scholar
  14. 14.
    Milstein D, Stille JK (1979) Palladium-catalyzed coupling of tetraorganotin compounds with aryl and benzyl halides. Synthetic utility and mechanism. J Am Chem Soc 101:4992–4998. CrossRefGoogle Scholar
  15. 15.
    Miyaura N, Suzuki A (1979) Stereoselective synthesis of arylated (E)-alkenes by the reaction of alk-1-enylboranes with aryl halides in the presence of palladium catalyst. J Chem Soc Chem Commun:866.
  16. 16.
    Reniers GLL, Brebbia CA (2011) Sustainable chemistry. WIT transactions on ecology and the environment, vol 154. WIT Press, Southampton/BostonGoogle Scholar
  17. 17.
    Shi W, Liu C, Lei A (2011) Transition-metal catalyzed oxidative cross-coupling reactions to form C-C bonds involving organometallic reagents as nucleophiles. Chem Soc Rev 40:2761–2776. CrossRefGoogle Scholar
  18. 18.
    Stuart DR, Fagnou K (2007) The catalytic cross-coupling of unactivated arenes. Science 316:1172–1175. CrossRefPubMedGoogle Scholar
  19. 19.
    Wan X, Ma Z, Li B, Zhang K, Cao S, Zhang S, Shi Z (2006) Highly selective C-H functionalization/halogenation of acetanilide. J Am Chem Soc 128:7416–7417. CrossRefPubMedGoogle Scholar
  20. 20.
    Wang P, Zhao G, Wang Y, Lu Y (2017) MnTiO3-driven low-temperature oxidative coupling of methane over TiO2-doped Mn2O3-Na2WO4/SiO2 catalyst. Sci Adv 3:e1603180. CrossRefPubMedPubMedCentralGoogle Scholar
  21. 21.
    Zhao Y, Wang H, Hou X, Hu Y, Lei A, Zhang H, Zhu L (2006) Oxidative cross-coupling through double transmetallation: surprisingly high selectivity for palladium-catalyzed cross-coupling of alkylzinc and alkynylstannanes. J Am Chem Soc 128:15048–15049. CrossRefPubMedGoogle Scholar

Copyright information

© Springer-Verlag GmbH Germany, part of Springer Nature 2019

Authors and Affiliations

  1. 1.State Key Laboratory for Oxo Synthesis and Selective OxidationSuzhou Research Institute of LICP, Lanzhou Institute of Chemical Physics (LICP), Chinese Academy of SciencesLanzhouChina

Personalised recommendations