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Alkyl- or Arylthiolation of Aryl Iodide via Cleavage of the S−S Bond of Disulfide Compound by Nickel Catalyst and Zinc

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Nobukazu Taniguchi

Department of Chemistry, Fukushima Medical University, Fukushima 960-1295, Japan %taniguti@fmu.ac.jp

J. Org. Chem., 2004, 69 (20), pp 6904–6906

DOI: 10.1021/jo040184q

Publication Date (Web): August 27, 2004

Section:

Benzene, Its Derivatives, and Condensed Benzenoid Compounds

Abstract

Various aryl sulfides can be synthesized by nickel-catalyzed alkyl- or arylthiolation of aryl iodide with a disulfide compound. This reaction produces Ni(0) from NiBr₂−bpy by the reduction with zinc, and this generated complex works as an activating species to convert ArI into ArSR under neutral conditions. Furthermore, this system enables the use of two RS groups in (RS)₂.

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