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Efficient recyclable CuI-nanoparticle-catalyzed S-arylation of thiols with aryl halides on water under mild conditions.

Organic & biomolecular chemistry (2012-02-23)
Hua-Jian Xu, Yu-Feng Liang, Xin-Feng Zhou, Yi-Si Feng
RÉSUMÉ

CuI nanoparticles efficiently catalyzed the C-S cross coupling of aryl and alkyl thiols with aryl halides in the absence of ligands on water under mild conditions. A wide range of diaryl sulfides and aryl alkyl sulfides are synthesized in good to excellent yields utilizing this protocol. This procedure is particularly noteworthy given its mild conditions, avoiding the undesired formation of disulfides through oxidation of thiols. The recovery and successful reutilization of the catalyst is described. Furthermore, the directed synthesis of bisarylated product is presented.

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Sigma-Aldrich
Copper(I) iodide, 98%
Sigma-Aldrich
Copper(I) iodide, 99.999% trace metals basis
Sigma-Aldrich
Copper(I) iodide, purum, ≥99.5%
Sigma-Aldrich
Dimethylglyoxime, ≥97.0% (TLC)