Pd-Catalyzed Double-Decarbonylative Aryl Sulfide Synthesis through Aryl Exchange between Amides and Thioesters

The reaction mechanism of Ni(COD)2 catalyzed hydrodesulfurization of aryl sulfide PhSMe with HSiMe3 has been predicted to have two competitive reaction pathways, with or without PhSMe spectator ligand, by using density functional theory methods.

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Fragmentation of aryl sulfide radical anions during aromatic SRN1 reactions

The Journal of Organic Chemistry ◽

10.1021/jo00913a026 ◽

1975 ◽

Vol 40 (25) ◽

pp. 3740-3743 ◽

Cited By ~ 34

Author(s):

J. F. Bunnett ◽

Xavier Creary

Keyword(s):

Radical Anions ◽

Aryl Sulfide

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Rotational Barriers, Charges, and Spin Densities in Alkyl Aryl Sulfide Radical Cations: A Density Functional Study

The Journal of Physical Chemistry A ◽

10.1021/jp0367124 ◽

2004 ◽

Vol 108 (12) ◽

pp. 2332-2338 ◽

Cited By ~ 13

Author(s):

Enrico Baciocchi ◽

Maria Francesca Gerini

Keyword(s):

Density Functional ◽

Radical Cations ◽

Functional Study ◽

Alkyl Aryl ◽

Density Functional Study ◽

Rotational Barriers ◽

Aryl Sulfide ◽

Spin Densities

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ChemInform Abstract: MECHANISMUS DER SULFILIMIN-BLDG. 3. MITT. KINETIK DER RK. EINIGER METHYL-ARYL-SULFIDE MIT CHLORAMIN-T

Chemischer Informationsdienst Organische Chemie ◽

10.1002/chin.197014126 ◽

1970 ◽

Vol 1 (14) ◽

pp. no-no

Author(s):

F. RUFF ◽

A. KUCSMAN

Keyword(s):

Aryl Sulfide

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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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