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 |

    A common problem with double C–H activation/cross-coupling is the formation of homocoupled products. Here, the authors show that an ionic group on one reagent during Fe catalysed cross-couplings can lead to a clearly defined order of C–H activation and hence the avoidance of homocoupled side-products.

    • Takahiro Doba
    • , Tatsuaki Matsubara
    • , Laurean Ilies
    • , Rui Shang
    •  & Eiichi Nakamura
    Nature Catalysis 2, 400-406
  • Research |

    While organolithium and organomagnesium compounds have well developed methods in organic chemistry, organosodium compounds are much less widely used. Here a method to generate organosodium compounds from aryl chlorides and (hetero)arenes is reported, along with a demonstration of their use in cross-coupling reactions.

    • Sobi Asako
    • , Hirotaka Nakajima
    •  & Kazuhiko Takai
    Nature Catalysis 2, 297-303
  • 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

News and Comment

  • Comments and Opinion |

    Radical intermediates are key species in many chemical transformations. Recent advances have provided a new suite of selective radical alkylation reactions. This Comment highlights pioneering studies using alkyl amines that act as radical precursors in a number of catalytic processes by their conversion to alkylpyridinium salts.

    • Duanyang Kong
    • , Patrick J. Moon
    •  & Rylan J. Lundgren
    Nature Catalysis 2, 473-476
  • 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