Ni-Catalyzed Aryl Sulfide Synthesis through an Aryl Exchange Reaction

10.26434/chemrxiv.14462376.v1 ◽

2021 ◽

Author(s):

Ryota Isshiki ◽

Miki B. Kurosawa ◽

Kei Muto ◽

Junichiro Yamaguchi

Keyword(s):

Exchange Reaction ◽

Ligand Exchange ◽

Aryl Halides ◽

Mechanistic Studies ◽

Aromatic Esters ◽

Oxidative Additions ◽

Aryl Sulfides ◽

Aryl Sulfide

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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Ni-Catalyzed Aryl Sulfide Synthesis through an Aryl Exchange Reaction

10.26434/chemrxiv.14462376 ◽

2021 ◽

Author(s):

Ryota Isshiki ◽

Miki B. Kurosawa ◽

Kei Muto ◽

Junichiro Yamaguchi

Keyword(s):

Exchange Reaction ◽

Ligand Exchange ◽

Aryl Halides ◽

Mechanistic Studies ◽

Aromatic Esters ◽

Oxidative Additions ◽

Aryl Sulfides ◽

Aryl Sulfide

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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Pyridyl disulfide-based thiol–disulfide exchange reaction: shaping the design of redox-responsive polymeric materials

Polymer Chemistry ◽

10.1039/d0py01215g ◽

2020 ◽

Vol 11 (48) ◽

pp. 7603-7624

Author(s):

Ismail Altinbasak ◽

Mehmet Arslan ◽

Rana Sanyal ◽

Amitav Sanyal

Keyword(s):

Exchange Reaction ◽

Functional Materials ◽

Polymeric Materials ◽

Disulfide Exchange ◽

Redox Responsive ◽

Synthetic Approaches

This review provides an overview of synthetic approaches utilized to incorporate the thiol-reactive pyridyl-disulfide motif into various polymeric materials, and briefly highlights its utilization to obtain functional materials.

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Photoassisted Production of O2-• and H2 in Aqueous Medium Stimulated by Polythiophene in ZSM-5 Zeolite Channels

Collection of Czechoslovak Chemical Communications ◽

10.1135/cccc19990149 ◽

1999 ◽

Vol 64 (1) ◽

pp. 149-156 ◽

Cited By ~ 7

Author(s):

Gabriel Čík ◽

František Šeršeň ◽

Alena Bumbálová

Keyword(s):

Reactive Oxygen Species ◽

Ion Exchange ◽

Visible Light ◽

Aqueous Medium ◽

Exchange Reaction ◽

Epr Spectroscopy ◽

Reactive Oxygen ◽

Oxygen Species ◽

Water Reduction ◽

Ion Exchange Reaction

The formation of reactive oxygen species due to irradiation by a visible light of the polythiophene deposited in ZSM-5 zeolite channels in aqueous medium has been studied. Polymerization of thiophene was carried out in zeolite channels after the ion-exchange reaction of Na+ for Fe3+. By means of EPR spectroscopy, the temporarily generated 1O2 in irradiated aqueous medium was proved. The formation of O2-• was confirmed by the reduction of Fe3+-cytochrome c. Irradiation led to the water reduction to hydrogen.

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