4.8 Article

Visible light mediated metal-free thiol-yne click reaction

Journal

CHEMICAL SCIENCE
Volume 7, Issue 11, Pages 6740-6745

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/c6sc02132h

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Funding

  1. Russian Science Foundation (RSF) [14-13-01030]
  2. Russian Science Foundation [14-13-01030] Funding Source: Russian Science Foundation

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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.

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