Jump to main content
Jump to site search

Issue 10, 2017
Previous Article Next Article

Copper-catalyzed cyanothiolation to incorporate a sulfur-substituted quaternary carbon center

Author affiliations

Abstract

Sulfur-containing nitriles have important research value in the life sciences due to their diverse biological activities resulting from the sulfur and cyano functional groups. Herein, a copper-catalyzed cyanothiolation of N-tosylhydrazones with thiocyanates to generate α-arylthioalkanenitriles bearing sulfur-substituted quaternary carbon center atoms has been described. This novel protocol involves the procedure of copper carbene species promoting S–CN bond cleavage and C–CN/C–S bond reconstruction to introduce both sulfur and cyano groups onto a single carbon center. This cyanothiolation reaction will greatly enhance the synthetic utility of carbenoid species as new entries for the construction of diverse heteroatom-containing nitriles via cyanofunctionalization of metal–carbene species.

Graphical abstract: Copper-catalyzed cyanothiolation to incorporate a sulfur-substituted quaternary carbon center

Back to tab navigation

Supplementary files

Publication details

The article was received on 29 Jun 2017, accepted on 15 Aug 2017 and first published on 15 Aug 2017


Article type: Edge Article
DOI: 10.1039/C7SC02867A
Citation: Chem. Sci., 2017,8, 7047-7051
  • Open access: Creative Commons BY license
  •   Request permissions

    Copper-catalyzed cyanothiolation to incorporate a sulfur-substituted quaternary carbon center

    Y. Huang, X. Li, X. Wang, Y. Yu, J. Zheng, W. Wu and H. Jiang, Chem. Sci., 2017, 8, 7047
    DOI: 10.1039/C7SC02867A

    This article is licensed under a Creative Commons Attribution 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.

    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