Cross-coupling reactions

Cross-coupling reactions are those in which two different starting materials, each of which is usually endowed with an activating group, are reacted together with the aid of a metal catalyst. The result is the loss of the two activating groups and the formation of a new covalent bond between the remaining fragments.

Latest Research and Reviews

  • Research | | open

    The mechanism for nickel-catalyzed catalyst transfer polycondensation of thiophenes to polythiophenes. Here the authors show experimental and computational evidence of structurally characterized square planar η2-Ni(0)–thiophene species and their relevance to the mechanism of catalyst transfer polycondensation.

    • Weiying He
    • , Brian O. Patrick
    •  & Pierre Kennepohl
  • Research |

    Cross-coupling of aryl compounds is one of the most powerful carbon–carbon bond forming reactions available, and typically involves the use of expensive and scarce palladium salts. Here Bedford and co-workers show that iron can be an effective catalyst for Suzuki biaryl couplings.

    • Harry M. O’Brien
    • , Mattia Manzotti
    • , Roman D. Abrams
    • , David Elorriaga
    • , Hazel A. Sparkes
    • , Sean A. Davis
    •  & Robin B. Bedford
    Nature Catalysis 1, 429-437
  • Research | | open

    Catalysis involving Au(I)/Au(III) cycles are notoriously hampered by the reluctance of Au(I) towards oxidative addition. Here, the authors show that an hemilabile bidentate ligand promotes oxidative addition of aryl halides to Au(I) and the catalytic formation of biaryl coupling products.

    • Abdallah Zeineddine
    • , Laura Estévez
    • , Sonia Mallet-Ladeira
    • , Karinne Miqueu
    • , Abderrahmane Amgoune
    •  & Didier Bourissou
  • Reviews |

    Elaborate molecules can be assembled in a relatively mild manner through organic cross-coupling reactions, with those mediated by group 10 metal complexes being particularly useful. This Review covers the development of nickel and palladium precatalysts, comparing state-of-the-art systems and offering design principles for future technologies.

    • Nilay Hazari
    • , Patrick R. Melvin
    •  & Megan Mohadjer Beromi

News and Comment

  • News and Views |

    Although the replacement of palladium with iron in metal-catalysed cross-couplings continues apace, the Suzuki synthesis of biaryls — arguably the most widely used class of such C–C bond formations — has remained elusive. Now, by use of a π-coordinating directing group, another step has been taken toward iron-catalysed Suzuki reactions.

    • Guojiao Wu
    •  & Axel Jacobi von Wangelin
    Nature Catalysis 1, 377-378
  • News and Views |

    Cross-coupling between a racemic secondary alkyl halide and an alkyl borane to produce an enantioenriched alkyl–alkyl product is one of the final substrate combinations to succumb to the synthetically powerful Suzuki–Miyaura methodology.

    • Ben W. Glasspoole
    •  & Cathleen M. Crudden
    Nature Chemistry 3, 912-913
  • Editorial |

    The 2010 Nobel Prize for Chemistry rewards a family of techniques for forging carbon-carbon bonds that have already helped to create new organic materials.