Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Nickel-Catalyzed Coupling of Arenesulfonates with Primary Alkylmagnesium Halides

  • Cho, Chul-Hee (School of Chemical & Materials Engineering, Chung-Ang University) ;
  • Sun, Myung-Chul (School of Chemical & Materials Engineering, Chung-Ang University) ;
  • Park, Kwang-Yong (School of Chemical & Materials Engineering, Chung-Ang University)
  • Published : 2005.09.20
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Abstract

Neopentyl arenesulfonates reacted with primary alkylmagnesium halides in the presence of $(PPh_3)_2NiCl_2$ to produce the corresponding alkylarenes. The efficiency of this coupling reaction considerably depends on the nature of catalyst and solvent. Highest yield was obtained by using three equivalents of Grignard reagent to a mixture of $(PPh_3)_2NiCl_2$ and arenesulfonate in refluxing $Et_2O$. This reaction represents a novel method allowing the efficient and creative substitution of sulfur-containing groups in aromatic compounds. It also shows that the alkyloxysulfonyl group might be a suitable alternative to halides and triflate in some circumstances.

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References

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