Visible Light Mediated Metal-free Thiol-yne Click Reaction

Overview

Journal Chem Sci

Publisher Royal Society of Chemistry

Specialty Chemistry

Date 2017 Apr 29

PMID 28451118

Citations 19

Authors

Sergey S Zalesskiy

Nikita S Shlapakov

Valentine P Ananikov

Affiliations

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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.

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