One-Pot Copper-Catalysed Thioetherification of Aryl Halides Using Alcohols and Lawesson's Reagent in Diglyme

A new protocol for the thioetherification of structurally varied alcohols with aryl halides using Lawesson's reagent, catalysed by copper(I) iodide, and using diglyme as a safe solvent was developed. Using this method, the reactions of aryl halides proceeded efficiently, and the desired sulfide...

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Veröffentlicht in:European journal of organic chemistry 2015-07, Vol.2015 (19), p.4162-4167
1. Verfasser: Gholinejad, Mohammad
Format: Artikel
Sprache:eng
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Zusammenfassung:A new protocol for the thioetherification of structurally varied alcohols with aryl halides using Lawesson's reagent, catalysed by copper(I) iodide, and using diglyme as a safe solvent was developed. Using this method, the reactions of aryl halides proceeded efficiently, and the desired sulfides were obtained in high to excellent yields. The method uses alcohols as starting materials, which is a significant advantage over methods that start from thiols. Alcohols are widely commercially available in a much greater structural diversity than thiols, and they are also nontoxic and not foul‐smelling. A reaction mechanism was proposed. A copper‐catalysed method for the thioetherification of alcohols with aryl halides using Lawesson's reagent was developed.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201500256