Copper-Catalyzed Double S-Arylation of Potassium Thioacetate with Dibenziodolium Triflates: Facile Synthesis of Unsymmetrical Dibenzothiophenes
Much interest has been paid to cyclic diaryliodonium salts as bis(electrophile)s in transition-metal-catalyzed annulation reactions to produce polycyclic (hetero)aromatic hydrocarbons. Herein, we report that dibenziodolium triflates smoothly react with potassium thioacetate in the presence of CuCl2in THF or DMSO at 100–110 °C to afford the corresponding dibenzothiophenes in good-to-high yields. The coupling reaction tolerates reactive functional groups such as chloro and cyano and serves as a facile and reliable method for the synthesis of unsymmetrical dibenzothiophenes.
N-Benzyldithiocarbamate Salts as Sulfur Sources to Access Tricyclic Thioheterocycles Mediated by Copper Species
Using an easily prepared triethylammonium N-benzyldithiocarbamate salt as a sulfur source, a dual C?S functionalization of cyclic diaryliodoniums to form tricyclic thioheterocycles is realized. Our method uses the readily available copper sulfate to accelerate the chemical transformation under mild conditions. A broad range of cyclic diaryliodoniums with a ring size from 5- to 7-membered can be employed to gain a quick access to tricyclic thioheterocycles including dibenzothiophenes, thioxanthenes, and phenoxathiines. (Figure presented.).
Palladium catalyzed aryl(alkyl)thiolation of unactivated arenes
A general palladium-catalyzed aryl(alkyl)thiolation of various substituted unactivated arenes is accomplished for the synthesis of diverse unsymmetrical diaryl(alkyl) sulfides in good yield employing electrophilic sulfur reagent 6 derived from succinimide. The developed strategy was coupled with intramolecular arylation of a C-H bond to afford dibenzothiphene derivatives, an important moiety in material science as organic semiconductors.
Saravanan, Perumal,Anbarasan, Pazhamalai
p. 848 - 851
(2014/03/21)
A simple and efficient synthesis of dibenzothiophene via BF 3·OEt2-promoted intramolecular annulation
A simple and efficient protocol promoted by BF3·OEt 2 for synthesizing functionalized dibenzothiophenes (DBTs) has been demonstrated. The annulation condition can tolerate a variety of functional groups. Georg Thieme Verlag Stuttgart · New York.
Shang, Xiaobo,Chen, Wanzhi,Yao, Yingming
p. 851 - 854
(2013/05/23)
The Synthesis of All of the Dimethyldibenzothiophenes and Monoethyldibenzothiophenes
The synthesis of all four isomers of the monoethyldibenzothiophenes and all of the sixteen isomers of the dimethyldibenzothiophenes has been accomplished.
Tedjamulia, Marvin L.,Tominaga, Yoshinori,Castle, Raymond N.
p. 1485 - 1495
(2007/10/02)
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