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Decarbonylative organoboron cross-coupling of esters by nickel catalysis

Author

Listed:
  • Kei Muto

    (Institute of Transformative Bio-Molecules (WPI-ITbM) and Graduate School of Science, Nagoya University)

  • Junichiro Yamaguchi

    (Institute of Transformative Bio-Molecules (WPI-ITbM) and Graduate School of Science, Nagoya University)

  • Djamaladdin G. Musaev

    (Emory University)

  • Kenichiro Itami

    (Institute of Transformative Bio-Molecules (WPI-ITbM) and Graduate School of Science, Nagoya University
    JST-ERATO, Itami Molecular Nanocarbon Project, Nagoya University)

Abstract

The Suzuki–Miyaura cross-coupling is a metal-catalysed reaction in which boron-based nucleophiles and halide-based electrophiles are reacted to form a single molecule. This is one of the most reliable tools in synthetic chemistry, and is extensively used in the synthesis of pharmaceuticals, agrochemicals and organic materials. Herein, we report a significant advance in the choice of electrophilic coupling partner in this reaction. With a user-friendly and inexpensive nickel catalyst, a range of phenyl esters of aromatic, heteroaromatic and aliphatic carboxylic acids react with boronic acids in a decarbonylative manner. Overall, phenyl ester moieties function as leaving groups. Theoretical calculations uncovered key mechanistic features of this unusual decarbonylative coupling. Since extraordinary numbers of ester-containing molecules are available both commercially and synthetically, this new ‘ester’ cross-coupling should find significant use in synthetic chemistry as an alternative to the standard halide-based Suzuki–Miyaura coupling.

Suggested Citation

  • Kei Muto & Junichiro Yamaguchi & Djamaladdin G. Musaev & Kenichiro Itami, 2015. "Decarbonylative organoboron cross-coupling of esters by nickel catalysis," Nature Communications, Nature, vol. 6(1), pages 1-8, November.
    • Handle: RePEc:nat:natcom:v:6:y:2015:i:1:d:10.1038_ncomms8508
    DOI: 10.1038/ncomms8508
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    Cited by:

    1. Geun Seok Lee & Beomsoon Park & Soon Hyeok Hong, 2022. "Stereoretentive cross-coupling of chiral amino acid chlorides and hydrocarbons through mechanistically controlled Ni/Ir photoredox catalysis," Nature Communications, Nature, vol. 13(1), pages 1-11, December.

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