Ni-Catalyzed Aryl Sulfide Synthesis through an Aryl Exchange Reaction

Ryota Isshiki, Miki B. Kurosawa, Kei Muto, Junichiro Yamaguchi*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

Abstract

A Ni-catalyzed aryl sulfide synthesis through an aryl exchange reaction between aryl sulfides and a variety of aryl electrophiles was developed. By using 2-pyridyl sulfide as a sulfide donor, this reaction achieved the synthesis of aryl sulfides without using odorous and toxic thiols. The use of a Ni/dcypt catalyst capable of cleaving and forming aryl-S bonds was important for the aryl exchange reaction between 2-pyridyl sulfides and aryl electrophiles, which include aromatic esters, arenol derivatives, and aryl halides. Mechanistic studies revealed that Ni/dcypt can simultaneously undergo oxidative additions of aryl sulfides and aromatic esters, followed by ligand exchange between the generated aryl-Ni-SR and aryl-Ni-OAr species to furnish aryl exchanged compounds.

Original languageEnglish
Pages (from-to)10333-10340
Number of pages8
JournalJournal of the American Chemical Society
Volume143
Issue number27
DOIs
Publication statusPublished - 2021 Jul 14

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

Fingerprint

Dive into the research topics of 'Ni-Catalyzed Aryl Sulfide Synthesis through an Aryl Exchange Reaction'. Together they form a unique fingerprint.

Cite this