Jump to main content
Jump to site search

Issue 11, 2016
Previous Article Next Article

Visible light mediated metal-free thiol–yne click reaction

Author affiliations

Abstract

The carbon–sulfur bond formation reaction is of paramount importance for functionalized materials design, as well as for biochemical applications. The use of expensive metal-based catalysts and the consequent contamination with trace metal impurities are challenging drawbacks of the existing methodologies. Here, we describe the first environmentally friendly metal-free photoredox pathway to the thiol–yne click reaction. Using Eosin Y as a cheap and readily available catalyst, C–S coupling products were obtained in high yields (up to 91%) and excellent selectivity (up to 60 : 1). A 3D-printed photoreactor was developed to create arrays of parallel reactions with temperature stabilization to improve the performance of the catalytic system.

Graphical abstract: Visible light mediated metal-free thiol–yne click reaction

Back to tab navigation

Supplementary files

Publication details

The article was received on 14 May 2016, accepted on 08 Jul 2016 and first published on 12 Jul 2016


Article type: Edge Article
DOI: 10.1039/C6SC02132H
Citation: Chem. Sci., 2016,7, 6740-6745
  • Open access: Creative Commons BY-NC license
  •   Request permissions

    Visible light mediated metal-free thiol–yne click reaction

    S. S. Zalesskiy, N. S. Shlapakov and V. P. Ananikov, Chem. Sci., 2016, 7, 6740
    DOI: 10.1039/C6SC02132H

    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