Nickel(II)-Mediated C−S Cross-Coupling Between Thiols and ortho-Substituted Arylboronic Acid

Kengo Hanaya, Hiroyoshi Ohtsu, Masaki Kawano, Shuhei Higashibayashi, Takeshi Sugai

Research output: Contribution to journalArticlepeer-review

Abstract

Herein, we report a C−S cross-coupling reaction between alkyl thiols or aryl thiols and ortho-substituted arylboronic acids that proceeds in the presence of an inexpensive and ligand-free NiCl2 ⋅ 6H2O salt and N-methylmorpholine, a weak base, at 25 °C in air. The presence of coordinating and electron-withdrawing groups at the ortho-position of the arylboronic acids played a crucial role in determining the efficiency of the reaction. X-ray crystallographic analysis revealed that the [NiCl2(DMF)2(H2O)2] complex was formed in-situ. The complex is an excellent precursor of the active nickel species. The reaction offers an extremely mild and operationally convenient method to access a wide variety of alkyl aryl sulfides and diaryl sulfides without using expensive transition metals, such as palladium, gold, and rhodium, and specialized and expensive ligands.

Original languageEnglish
Pages (from-to)582-587
Number of pages6
JournalAsian Journal of Organic Chemistry
Volume10
Issue number3
DOIs
Publication statusPublished - 2021 Mar

Keywords

  • Boron
  • Cross-coupling
  • Nickel
  • Sulfur
  • Synthetic method

ASJC Scopus subject areas

  • Organic Chemistry

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