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Photochemical Organocatalytic Synthesis of Thioethers from Aryl Chlorides and Alcohols by Shuo Wu; Thomas Hin-Fung Wong; Paolo Righi; Paolo Melchiorre is a Chemistry article available to read on EtoBox.

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Thioethers, often found in pharmaceuticals and natural compounds, typically involve metal cross-coupling reactions, high temperatures, and the use of disagreeable thiols for their synthesis. Here we present a straightforward, thiol-free organocatalytic protocol that uses mild conditions to stitch together inexpensive alcohols and aryl chlorides, yielding a diverse array of aryl alkyl thioethers. Central to this approach was the discovery that tetramethylthiourea can serve as a simple sulfur source upon intercepting photochemically generated aryl radicals. To form radicals, we used a readily available indole thiolate organocatalyst that, when excited with 405 nm light, gained a strongly reducing power, enabling the activation of typically unreactive aryl chlorides via singleelectron transfer. Radical trapping by the thiourea, followed by an alcohol attack via a polar path, resulted in the formation of thioether products. T hioethers are prevalent in natural products and pharma- ceuticals 1 with bioactivity against diseases like cancer, HIV, and Alzheimer's. Devising synthetic methods for their efficient

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Author

Shuo Wu; Thomas Hin-Fung Wong; Paolo Righi; Paolo Melchiorre

Publisher

American Chemical Society (ACS)

Published

2024

Language

EN

Field

Chemistry (Physical Sciences)