35550-81-3Relevant articles and documents
Nickel-Catalyzed Difunctionalization of Alkynyl Bromides with Thiosulfonates and N -Arylthio Succinimides: A Convenient Synthesis of 1,2-Thiosulfonylethenes and 1,1-Dithioethenes
Kumari, Arram Haritha,Kumar, Jangam Jagadesh,Krishna, Gamidi Rama,Reddy, Raju Jannapu
, p. 2850 - 2864 (2021/05/18)
An efficient nickel-catalyzed vicinal thiosulfonylation of 1-bromoalkynes with thiosulfonates in the presence of cesium carbonate is described. An operationally simple and highly regioselective atom transfer radical addition (ATRA) of alkynyl bromides provides a wide range of (E)-1,2-thiosulfonylethenes (α-aryl-β-thioarylvinyl sulfones) in moderate to high yields. The extensive substrate scope of both alkynyl bromides and thiosulfonates is explored with a broad range of functional groups. Indole-derived 1,1-bromoalkenes were also successfully explored in this 1,2-thiosulfonylation process. Moreover, the nickel-catalyzed geminal -dithiolation of alkynyl bromides with N -arylthio succinimides provides 1,1-dithioalkenes in high yields. The present protocol is reliable on gram scale, and a sequential one-pot bromination and thiosulfonylation of phenylacetylene is achieved in a scale-up synthesis. Following control experiments, a plausible mechanism is proposed to rationalize the experimental outcome and the vicinal thio-sulfonylation.
A Simplified Protocol for the Stereospecific Nickel-Catalyzed C-S Vinylation Using NiX 2 Salts and Alkyl Phosphites
Larin, Egor M.,Lautens, Mark,Marchese, Austin D.,Mirabi, Bijan
, p. 311 - 319 (2019/12/28)
A Ni-catalyzed C-S cross-coupling using only NiI 2 (0.5-2.5 molpercent) and P(O i Pr) 3 (2.0-10.0 molpercent) is reported. Using an air-stable Ni(II) precatalyst, and a cheap and commercially available ligand, a scalable and robust method was developed to cross-couple various thiophenols and styryl bromides, including some sterically encumbered thiols, an α-bromocinnamaldehyde as well as a thiolation-cyclization.
Hollow nanoshell-sphere Fe@Fe/Pd reactors: a magnetically recoverable catalyst for the Csp–S cross-coupling reactions in water
Abadi, Parvaneh Ghaderi-Shekhi,Rafiee, Ezzat,Joshaghani, Mohammad
, p. 1513 - 1525 (2018/06/21)
The hollow Pd–PVP–Fe nanosphere and Fe–PVP nanoparticle catalysts were synthesized by thermal method. Mixing of two metallic nanocatalysts was applied in the Csp–S cross-coupling reactions between diphenyl disulfide and phenylacetylene under mi
Thiol radical addition to alkynes. Sulfanyl radical addition and hydrogen atom abstraction relative reaction rates
Melandri, Daniela,Montevecchi, Pier Carlo,Navacchia, Maria Luisa
, p. 12227 - 12236 (2007/10/03)
2-(Toluenesulfanyl)- 1 and 2-(benzenesulfanyl)-phenylacetylene 10 reacted with benzenethiol and toluenethiol, respectively, in the presence of AIBN at 84 and 154°C to give products deriving from vinyl radicals 2 which undergo hydrogen abstraction reaction
A Direct Formation of Alkenyl Chalcogenides from Nonactivated Alkenyl Halides and Diorganyl Dichalcogenides under Neutral Conditions
Ogawa, Takuji,Hayami, Kazuo,Suzuki, Hitomi
, p. 769 - 772 (2007/10/02)
Alkenyl sulfides and selenides were easily obtained in moderate to good yields by heating the corresponding bromides with diorganyl disulfides or diselenides in hexamethylphosphoric triamide with or without copper(I) iodide as a promoter.
ELIMINATION OF THIOPHENOL FROM PHENYL ORTHOTHIOESTERS IN THE MASS SPECTROMETER AND NOVEL REARRANGEMENT OF KETENE THIOACETALS UPON ELECTRON IMPACT
El-Khawaga, Ahmed M.,El-Zohry, Maher F.
, p. 179 - 183 (2007/10/02)
The mass spectra of four selected phenyl orthothioesters (1-4) have been measured.The obtained spectra revealed the conversion of the compounds (1-4) into ketene thioacetals (5-8) via the elimination of thiophenol in the mass spectrometer.The thermal natu
Synthesis of Vinyl Selenides or Sulfides and Ketene Selenoacetals or Thioacetals by Nickel(II) Vinylation of Sodium Benzeneselenolate or Benzenethiolate
Cristau, H. J.,Chabaud, B.,Labaudiniere, R.,Christol, H.
, p. 875 - 878 (2007/10/02)
The substitution of bromine atom on a double bond by benzeneselenolate or benzenethiolate anions is catalyzed by the bis(pyridine)nickel bromide complex.Various alkenyl selenides or sulfides and seleno- or thio acetals are prepared in good to excellent yi
New synthetic routes to vinyl sulfides, ketene thioacetals and their seleno analogues from carbonyl compounds
Denis,Desauvage,Hevesi,Krief
, p. 4009 - 4012 (2007/10/02)
Title compounds have been prepared from carbonyl compounds by formal removal of hydroxyl and sulfenyl or hydroxyl and selenyl moieties from the corresponding functionalized β-hydroxysulfides or β-hydroxyselenides.
