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Visible Light-Mediated Thiolation of Substituted 1,4-Naphthoquinones Using Eosin y as a Photoredox Catalyst
Published in American Chemical Society
2022
Volume: 87
   
Issue: 5
Pages: 3195 - 3201
Abstract
In the presence of eosin Y, a visible light-induced one-step procedure (isolated yield of ≥75%) for thiolation of substituted 1,4-naphthoquinones using various aromatic and aliphatic thiols at room temperature is described herein. The rate-determining step of the reaction is thiyl radical generation, and the radical was characterized by high-resolution mass spectrometry. Cost effectiveness, operational simplicity, a short reaction time, high atom economy, and a very good yield make this photoredox-mediated process a useful alternative to the transition metal (e.g., Cu, Ag, and Pd)-catalyzed coupling reaction of quinones with thiols or disulfides. © 2022 American Chemical Society. All rights reserved.
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Published in American Chemical Society
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