Visible-Light-Induced Desulfurative Coupling of Alkyl Benzothiazolyl Sulfides with Electron-Deficient Alkenes/Alkynes: Dual Role of Base-Activated Hantzsch Esters
Dr. Tetsuya Sengoku, Koki Matsune, Takuma Shimotori, Nagisa Kikuchi, Haruto Hijikata, Shun Nishioka, Reo Takahashi
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引用次数: 0
Abstract
Hantzsch ester (HEH) is a bench-stable compound used in hydrogenation and photoinduced reactions, where it acts as a photoreductant and an electron donor. In this study, we describe a new use of this classical reductant in the visible-light-induced desulfurative coupling of alkyl benzothiazolyl sulfides with electron-deficient alkenes/alkynes via activation with base additives. C(sp3)─S scission is achieved through catalyst-free HEH anion-mediated reactions and organo-photocatalysis. The synthetic utility is illustrated with several examples of derivatization of natural products, including monosaccharides. In addition, mechanistic investigations reveal that the HEH anion acts as a photoreductant in catalyst-free reactions and as a sacrificial reductant in the organo-photocatalysis.
期刊介绍：
With an impact factor of 4.495 (2018), ChemCatChem is one of the premier journals in the field of catalysis. The journal provides primary research papers and critical secondary information on heterogeneous, homogeneous and bio- and nanocatalysis. The journal is well placed to strengthen cross-communication within between these communities. Its authors and readers come from academia, the chemical industry, and government laboratories across the world. It is published on behalf of Chemistry Europe, an association of 16 European chemical societies, and is supported by the German Catalysis Society.
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