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Visible light mediated metal-free thiol-yne click reaction.

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.

SUBMITTER: Zalesskiy SS

PROVIDER: S-EPMC5355861 | biostudies-literature | 2016 Nov

REPOSITORIES: biostudies-literature

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Visible light mediated metal-free thiol-yne click reaction.

Zalesskiy Sergey S SS Shlapakov Nikita S NS Ananikov Valentine P VP

Chemical science 20160712 11

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 produc ...[more]

PMID: 28451118

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