Jump to main content
Jump to site search

Issue 16, 2019
Previous Article Next Article

Nickel-catalyzed C–N bond activation: activated primary amines as alkylating reagents in reductive cross-coupling

Author affiliations

Abstract

Nickel-catalyzed reductive cross coupling of activated primary amines with aryl halides under mild reaction conditions has been achieved for the first time. Due to the avoidance of stoichiometric organometallic reagents and external bases, the scope regarding both coupling partners is broad. Thus, a wide range of substrates, natural products and drugs with diverse functional groups are tolerated. Moreover, experimental mechanistic investigations and density functional theory (DFT) calculations in combination with wavefunction analysis have been performed to understand the catalytic cycle in more detail.

Graphical abstract: Nickel-catalyzed C–N bond activation: activated primary amines as alkylating reagents in reductive cross-coupling

Back to tab navigation

Supplementary files

Publication details

The article was received on 14 Feb 2019, accepted on 12 Mar 2019 and first published on 20 Mar 2019


Article type: Edge Article
DOI: 10.1039/C9SC00783K
Chem. Sci., 2019,10, 4430-4435
  • Open access: Creative Commons BY-NC license
    All publication charges for this article have been paid for by the Royal Society of Chemistry

  •   Request permissions

    Nickel-catalyzed C–N bond activation: activated primary amines as alkylating reagents in reductive cross-coupling

    H. Yue, C. Zhu, L. Shen, Q. Geng, K. J. Hock, T. Yuan, L. Cavallo and M. Rueping, Chem. Sci., 2019, 10, 4430
    DOI: 10.1039/C9SC00783K

    This article is licensed under a Creative Commons Attribution-NonCommercial 3.0 Unported Licence. Material from this article can be used in other publications provided that the correct acknowledgement is given with the reproduced material and it is not used for commercial purposes.

    Reproduced material should be attributed as follows:

    • For reproduction of material from NJC:
      [Original citation] - Published by The Royal Society of Chemistry (RSC) on behalf of the Centre National de la Recherche Scientifique (CNRS) and the RSC.
    • For reproduction of material from PCCP:
      [Original citation] - Published by the PCCP Owner Societies.
    • For reproduction of material from PPS:
      [Original citation] - Published by The Royal Society of Chemistry (RSC) on behalf of the European Society for Photobiology, the European Photochemistry Association, and RSC.
    • For reproduction of material from all other RSC journals:
      [Original citation] - Published by The Royal Society of Chemistry.

    Information about reproducing material from RSC articles with different licences is available on our Permission Requests page.

Search articles by author

Spotlight

Advertisements