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Copper-Catalyzed Thioetherification Reactions of Alkyl Halides, Triphenyltin Chloride, and Arylboronic Acids With Nitroarenes in the Presence of Sulfur Sources

Copper-Catalyzed Thioetherification Reactions of Alkyl Halides, Triphenyltin Chloride, and Arylboronic Acids With Nitroarenes in the Presence of Sulfur Sources

Abed Rostami, Amin Rostami, Arash Ghaderi

J Org Chem. 2015 Sep 4;80(17):8694-704.

PMID: 26272238

Abstract:

In this article, we report three odorless methods for the thioarylation and thioalkylation of different nitroarenes using alkyl halides (Br, Cl), triphenyltin chloride, and arylboronic acids as the coupling partners. Triphenyltin chloride is capable of delivering all of its phenyl groups to the product. Depending on the reaction, sodium thiosulfate pentahydrate (Na2S2O3·5H2O), S8/KF, and S8/NaOH systems are found to be effective sources of sulfur in the presence of copper salts. The use of green solvents, inexpensive catalysts, and user-friendly starting materials has made these methods interesting from a green chemistry standpoint.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP10102177-B	Sodium thiosulfate pentahydrate		10102-17-7	Price

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