Ni-Catalyzed Aryl Sulfide Synthesis through an Aryl Exchange Reaction

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Ni-Catalyzed Aryl Sulfide Synthesis through an Aryl Exchange Reaction

Isshiki, R.; Kurosawa, M. B.; Muto, K.; Yamaguchi, J.
J. Am. Chem. Soc. 2021, ASAP.

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.

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