- Ligand-Free CuI-Catalyzed Chemoselective S-Arylation of 2-Mercaptobenzimidazole with Aryl Iodides
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A practical and efficient strategy for the chemoselective C-S cross-coupling of 2-mercaptobenzimidazole derivatives with a range of substituted aryl iodides is described. Under the optimized conditions of 5 mol% CuI and 100 °C, a variety of S-arylated products were obtained in good to excellent yields (up to 92 %) without the need for assisting ligands.
- Tan, Bryan Yong-Hao,Teo, Yong-Chua
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supporting information
p. 2056 - 2060
(2018/09/18)
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- PHOTOCATALYST-FREE, LIGHT-INDUCED CARBON-SULFUR CROSS-COUPLING METHODS
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In one aspect, the invention provides a method of promoting a carbon-sulfur bond forming reaction. In certain embodiments, the reaction comprises cross-coupling of a(n) (hetero)aryl halide with a thiol to form the carbon-sulfur bond, wherein the method is promoted by light irradiation in the absence of a photocatalyst. In other embodiments, the cross-coupling reaction can be promoted through visible light irradiation, including sunlight.
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Paragraph 0100; 0191; 0192
(2019/01/10)
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- Visible-light-promoted C-S cross-coupling via intermolecular charge transfer
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Disclosed is a mild, scalable, visible-lightpromoted cross-coupling reaction between thiols and aryl halides for the construction of C-S bonds in the absence of both transition metal and photoredox catalysts. The scope of aryl halides and thiol partners includes over 60 examples and therefore provides an entry point into various aryl thioether building blocks of pharmaceutical interest. Furthermore, to demonstrate its utility, this C-S coupling protocol was applied in drug synthesis and latestage modifications of active pharmaceutical ingredients. UV-vis spectroscopy and time-dependent density functional theory calculations suggest that visible-lightpromoted intermolecular charge transfer within the thiolate-aryl halide electron donor-acceptor complex permits the reactivity in the absence of catalyst.
- Liu, Bin,Lim, Chern-Hooi,Miyake, Garret M.
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supporting information
p. 13616 - 13619
(2017/11/06)
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