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Ni-Catalyzed Aryl Sulfide Synthesis through an Aryl Exchange Reaction

preprint
submitted on 22.04.2021, 00:59 and posted on 22.04.2021, 13:07 by Ryota Isshiki, Miki B. Kurosawa, Kei Muto, Junichiro Yamaguchi
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.

Funding

JP19H02726

JP20H04829

JP19J23053

JPMJER1901

History

Email Address of Submitting Author

junyamaguchi@waseda.jp

Institution

Waseda University

Country

Japan

ORCID For Submitting Author

0000-0002-3896-5882

Declaration of Conflict of Interest

The authors declare no competing financial interest.

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