Synthesis of Aryl Sulfides by Metal‐Free Arylation of Thiols with Diaryliodonium Salts under Basic Conditions

2021 ◽  
Author(s):  
Sudeep Sarkar ◽  
Natalia Wojciechowska ◽  
Adam A. Rajkiewicz ◽  
Marcin Kalek
Keyword(s):  
Metal Free ◽  
Diaryliodonium Salts ◽  
Aryl Sulfides

scholarly journals Synthesis of Aryl Sulfides by Metal-Free Arylation of Thiols with Diaryliodonium Salts

2021 ◽  
Author(s):  
Sudeep Sarkar ◽  
Natalia Wojciechowska ◽  
Adam A. Rajkiewicz ◽  
Marcin Kalek
Keyword(s):  
Dft Calculations ◽  
Bond Formation ◽  
Reductive Elimination ◽  
Organic Base ◽  
Metal Free ◽  
Diaryliodonium Salts ◽  
Inner Sphere ◽  
Aryl Sulfides ◽  
Mechanism Of The Reaction

Metal-free arylation of thiols with diaryliodonium salts has been developed. The application of a strong organic base ena-bles the C–S bond formation under mild and experimentally simple conditions. The method allows for the synthesis of aryl sulfides containing a broad range of aryl groups from an array of thiols, including aryl, heteroaryl, and alkyl ones. The mechanism of the reaction was studied by DFT calculations, demonstrating that is follows the inner sphere pathway involv-ing the incipient formation of Ar2I(SR) intermediate, followed by the reductive elimination.

Rapid synthesis of aryl sulfides through metal-free C–S coupling of thioalcohols with diaryliodonium salts

2014 ◽  
Vol 55 (42) ◽  
pp. 5739-5741 ◽  
Author(s):  
Dawei Wang ◽  
Xin Yu ◽  
Keyan Zhao ◽  
Liang Li ◽  
Yuqiang Ding
Keyword(s):  
Rapid Synthesis ◽  
Metal Free ◽  
Diaryliodonium Salts ◽  
Aryl Sulfides

Safe and Metal-Free Synthesis of 1-Alkenyl Aryl Sulfides and Their Sulfones from Thiiranes and Diaryliodonium Salts

Synthesis ◽  
2018 ◽  
Vol 50 (12) ◽  
pp. 2407-2415 ◽  
Author(s):  
Jiaxi Xu ◽  
Jun Dong
Keyword(s):  
Reaction Mechanism ◽  
Ring Opening ◽  
Hydrogen Abstraction ◽  
Current Method ◽  
Performic Acid ◽  
Nucleophilic Attack ◽  
Safe Method ◽  
Metal Free ◽  
Diaryliodonium Salts ◽  
Aryl Sulfides

A series of 1-alkenyl aryl sulfides was synthesized from thiiranes and diaryliodonium salts in tetrahydrofuran in the presence of potassium tert-butoxide. The proposed reaction mechanism involves generation of benzynes from the diaryliodonium salts in the presence of the base. Then, nucleophilic attack of the benzynes by thiiranes, followed by hydrogen abstraction and ring opening of the generated thiiranium intermediates, provides the sulfides. These sulfides were further oxidized with performic acid to the corresponding sulfones. The current method provides a metal-free and safe method for the preparation of 1-alkenyl aryl sulfides and their sulfones.

ChemInform Abstract: Rapid Synthesis of Aryl Sulfides Through Metal-Free C-S Coupling of Thioalcohols with Diaryliodonium Salts.

ChemInform ◽  
2015 ◽  
Vol 46 (15) ◽  
pp. no-no
Author(s):  
Dawei Wang ◽  
Xin Yu ◽  
Keyan Zhao ◽  
Liang Li ◽  
Yuqiang Ding
Keyword(s):  
Rapid Synthesis ◽  
Metal Free ◽  
Diaryliodonium Salts ◽  
Aryl Sulfides

Transition Metal-Free O-Arylation of Quinoxalin-2-ones with Diaryliodonium Salts

Heterocycles ◽  
2021 ◽  
Vol 103 (1) ◽  
pp. 502
Author(s):  
Masami Kuriyama ◽  
Osamu Onomura ◽  
Yuki Mochizuki ◽  
Tsubasa Miyagi ◽  
Kosuke Yamamoto ◽  
...  
Keyword(s):  
Transition Metal ◽  
Metal Free ◽  
Diaryliodonium Salts

Transition metal-free base-promoted arylation of sulfenate anions with diaryliodonium salts

2019 ◽  
Vol 6 (1) ◽  
pp. 32-35 ◽  
Author(s):  
Lei Wang ◽  
Mingjie Chen ◽  
Junliang Zhang
Keyword(s):  
Transition Metal ◽  
Free Base ◽  
Metal Free ◽  
Diaryliodonium Salts

A base-promoted formal arylation of general sulfenate anions with diaryliodonium salts under transition-metal-free conditions has been described.

scholarly journals Heteroaryliodonium(III) Salts as Highly Reactive Electrophiles

2020 ◽  
Vol 8 ◽  
Author(s):  
Naoko Takenaga ◽  
Ravi Kumar ◽  
Toshifumi Dohi
Keyword(s):  
High Reactivity ◽  
Hypervalent Iodine ◽  
Metal Free ◽  
Diaryliodonium Salts ◽  
Metal Catalyzed ◽  
Synthetic Transformations

In recent years, the chemistry of heteroaryliodonium(III) salts has undergone significant developments. Heteroaryliodonium(III) salts have been found to be useful synthetic tools for the transfer of heteroaryl groups under metal-catalyzed and metal-free conditions for the preparation of functionalized heteroarene-containing compounds. Synthetic transformations mediated by these heteroaryliodonium(III) salts are classified into two categories: (1) reactions utilizing the high reactivity of the hypervalent iodine(III) species, and (2) reactions based on unique and new reactivities not observed in other types of conventional diaryliodonium salts. The latter feature is of particular interest and so has been intensively investigated in recent decades. This mini-review therefore aims to summarize the recent synthetic applications of heteroaryliodonium(III) salts as highly reactive electrophiles.

Metal-free photoinitiated controlled cationic polymerization of isopropyl vinyl ether using diaryliodonium salts

2019 ◽  
Vol 10 (9) ◽  
pp. 1056-1061 ◽  
Author(s):  
Tsuyoshi Nishikawa ◽  
Arihiro Kanazawa ◽  
Sadahito Aoshima
Keyword(s):  
Vinyl Ether ◽  
Cationic Polymerization ◽  
Metal Free ◽  
Diaryliodonium Salts

Metal-free photoinitiated controlled cationic polymerization of isopropyl vinyl ether proceeded via the spontaneous cleavage of the carbon–iodine bonds at the propagating ends.

ChemInform Abstract: Direct Metal-Free O-Arylation of Biginelli 4-Aryl-6-methyl-pyrimidine-2(1H)-one Derivatives Using Diaryliodonium Salts.

ChemInform ◽  
2015 ◽  
Vol 46 (15) ◽  
pp. no-no
Author(s):  
Prerana B. Thorat ◽  
Nitin A. Waghmode ◽  
Nandkishor N. Karade
Keyword(s):  
Metal Free ◽  
Diaryliodonium Salts
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