92023-43-3Relevant academic research and scientific papers
Phenyldithiocarbamates: Efficient Sulfuration Reagents in the Chan–Lam Coupling Reaction
Cheng, Yu,Liu, Xing,Dong, Zhi-Bing
, p. 815 - 820 (2018)
The Chan–Lam coupling reaction starting from phenyldithiocarbamates and phenylboronic acids is reported. To avoid using the volatile, hazardous, and foul-smelling thiols, which are sometimes expensive and not sufficiently available, phenyldithiocarbamates can be employed. They are demonstrated to be good sulfuration reagents in the Chan–Lam coupling to prepare biaryl sulfides. By using this protocol, dithiocarbamate substrates with a wide range of functional groups including electron-rich and electron-deficient ones are explored to obtain the desired substituted biaryl sulfides smoothly. This method is ligand-free, has a broad substrate scope, enables good yields, and is easy to perform. It provides a facile and convenient preparation of biaryl sulfides.
Nickel-Catalyzed C–S Coupling: Synthesis of Diaryl Sulfides Starting from Phenyldithiocarbamates and Iodobenzenes
Liu, Xing,Cao, Qiang,Xu, Wan,Zeng, Meng-Tian,Dong, Zhi-Bing
, p. 5795 - 5799 (2017/10/23)
A nickel-catalyzed C–S bond-formation protocol for the synthesis of diaryl sulfides is described. In a reaction catalyzed by NiCl2, phenyldithiocarbamates react with iodobenzenes to give diaryl sulfides smoothly in good to excellent yields (66–93 %). The catalyst is cheap, the reaction is easy to carry out, the substrate scope is broad, and the yields are good. Thus, this gives an alternative way to prepare diaryl sulfides.
Synthesis of Diverse o-Arylthio-Substituted Diaryl Ethers by Direct Oxythiolation of Arynes with Diaryl Sulfoxides Involving Migratory O-Arylation
Matsuzawa, Tsubasa,Uchida, Keisuke,Yoshida, Suguru,Hosoya, Takamitsu
supporting information, p. 5521 - 5524 (2017/10/25)
A diverse range of o-arylthio-substituted diaryl ethers has been synthesized by direct oxythiolation of arynes with diaryl sulfoxides that involves the formation of the C-O and C-S bonds followed by migratory O-arylation.
Carbon-sulfur bond formation catalyzed by [Pd(IPr*OMe) (cin)Cl] (cin = cinnamyl)
Bastug, Gulluzar,Nolan, Steven P.
supporting information, p. 9303 - 9308 (2013/10/08)
The newly prepared complex [Pd(IPr*OMe)(cin)(Cl)] provides high catalytic activity for carbon-sulfur cross-coupling reactions. Nonactivated and deactivated aryl halides were successfully coupled with a large variety of aryl- and alkylthiols using this well-defined palladium N-heterocyclic carbene (NHC) complex.
Recyclable heterogeneous supported copper-catalyzed coupling of thiols with aryl halides: base-controlled differential arylthiolation of bromoiodobenzenes
Bhadra, Sukalyan,Sreedhar, Bojja,Ranu, Brindaban C.
experimental part, p. 2369 - 2378 (2009/12/28)
Alumina-supported copper sulfate efficiently catalyzes the 5-arylation of aromatic, heteroaromatic and aliphatic thiols with aryl as well as heteroaryl halides under aerobic, ligand-free conditions. This protocol provides an easy access to a variety of thioethers as well as unsymmetrical bis-thioethers by base-controlled differential coupling of thiols with iodo- and bromo-substituents in an aromatic halide. The catalyst is inexpensive, non-air sensitive, environmentally friendly and recyclable.
Microwave-assisted simple and efficient ligand free copper nanoparticle catalyzed aryl-sulfur bond formation
Ranu, Brindaban C.,Saha, Amit,Jana, Ranjan
, p. 2690 - 2696 (2008/09/19)
A new protocol for the coupling of aryl iodides with thiophenols and alkanethiols catalyzed by copper nanoparticles under ligand-free condition has been developed. A variety of functionalized aryl sulfides are prepared in excellent yields under microwave irradiation for 5-7 min. A plausible radical mechanism has been suggested.
"β-cis-SAr effect" on decarbonylation from α,β-unsaturated acyl and aroyl complexes
Kato, Tomohiro,Kuniyasu, Hitoshi,Kajiura, Takamichi,Minami, Yasunori,Ohtaka, Atsushi,Kinomoto, Masanori,Terao, Jun,Kurosawa, Hideo,Kambe, Nobuaki
, p. 868 - 870 (2008/02/08)
Lone pair of heteroatom located at the β-cis position in α,β-unsaturated acyl and aroyl group 10 metal complexes dramatically facilitated the stoichiometric and catalytic decarbonylation reactions. The Royal Society of Chemistry 2006.
Preparation of optically active ortho-chloro- and ortho-bromophenyl sulfoxides
Imboden, Christoph,Renaud, Philippe
, p. 1051 - 1060 (2007/10/03)
The preparation of the diastereomerically pure menthyl (S)-2-chloro- and (S)-2-bromophenyl sulfinates by esterification of the corresponding sulfinic acids with (1R,2S,5R)-(-)-menthol and recrystallization/epimerization is reported. The two sulfinates have been converted into enantiomerically pure aryl, vinyl and alkyl sulfoxides by reaction with organomagnesium reagents. These sulfoxides are useful chiral auxiliaries to control the stereochemical outcome of radical reactions.
