Related Experiment Video
Updated: Mar 3, 2026

Metal-free Synthesis of Ynones from Acyl Chlorides and Potassium Alkynyltrifluoroborate Salts
Published on: February 24, 2015
Visible light mediated metal-free thiol-yne click reaction
Sergey S Zalesskiy1, Nikita S Shlapakov1, Valentine P Ananikov1
1Zelinsky Institute of Organic Chemistry , Russian Academy of Sciences , Leninsky prospekt, 47 , Moscow , 119991 , Russia .
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.
More Related Videos
Related Concept Videos
Preparation and Reactions of Thiols
Cycloaddition Reactions: MO Requirements for Photochemical Activation
Metal-Ligand Bonds
In these complexes, transition metals form coordinate covalent bonds, a kind of Lewis acid-base interaction in which both of the electrons in the bond are contributed by a donor (Lewis base) to an electron acceptor (Lewis acid). The Lewis acid in...
Preparation and Reactions of Sulfides
Thermal and Photochemical Electrocyclic Reactions: Overview
Reduction of Alkynes to trans-Alkenes: Sodium in Liquid Ammonia
When dissolved in liquid ammonia, an alkali metal, such as sodium,...

