18255-06-6Relevant articles and documents
Transition metal-free coupling reactions of benzylic trimethylammonium salts with di(hetero)aryl disulfides and diselenides
Li, Fuhai,Wang, Dan,Chen, Hongyi,He, Ze,Zhou, Lihong,Zeng, Qingle
, p. 13029 - 13032 (2020/11/07)
A new protocol was developed to synthesize (enantioenriched) thioethers and selenoethers from (chiral) benzylic trimethylammonium salts and di(hetero)aryl disulfides or diselenides. These syntheses were promoted by the presence of weak base and did not require the use of any transition metal, and resulted in the target products with good to excellent yields (72-94%). Using quaternary ammonium salts synthesized from enantiomerically enriched amines led to highly enantiopure benzylic thioethers and selenoethers (94-99% ee) with configurations reversed from those of their enantioenriched quaternary ammonium salts. This journal is
A highly efficient heterogeneous ruthenium(III)-catalyzed reaction of diaryl diselenides with alkyl halides leading to unsymmetrical diorganyl selenides
Chen, Qiurong,Wang, Pingping,Yan, Tao,Cai, Mingzhong
, p. 38 - 46 (2017/04/19)
A highly efficient heterogeneous ruthenium(III)-catalyzed reaction of diaryl diselenides with alkyl halides was achieved in DMF at 100?°C in the presence of 2?mol% of an MCM-41-immobilized bidentate nitrogen ruthenium(III) complex [MCM-41-2N-RuCl3] and zinc, yielding a variety of unsymmetrical diorganyl selenides in good to excellent yields. This new heterogeneous ruthenium catalyst can easily be prepared via a simple two-step procedure from commercially readily available and inexpensive reagents, and recovered by filtration of the reaction solution and recycled for at least eight times without a significant loss of activity.
A comparative study of Cu(II)-assisted vs Cu(II)-free chalcogenation on benzyl and 2°/3°-cycloalkyl moieties
Sahoo, Santosh K
, p. 2151 - 2157 (2016/01/12)
A relative synthetic strategy toward intermolecular oxidative C -Chalcogen bond formation of alkanes has been illustrated using both Cu(II) assisted vs Cu(II) free conditions. This led to construction of a comparative study of hydrocarbon benzylic and 2°/ 3°-cycloalkyl moieties bond sulfenylation and selenation protocol by the chalcogen sources, particularly sulfur and selenium, respectively. In addition, this protocol disclosed the auspicious formation of sp3 C-S coupling products over leading the sp3 C-N coupling products by using 2-mercaptobenzothiazole (MBT) substrates.
Metal-free sp3 C-H functionalization: A novel approach for the syntheses of selenide ethers and thioesters from methyl arenes
Badsara, Satpal Singh,Liu, Yi-Chen,Hsieh, Ping-An,Zeng, Jing-Wen,Lu, Shao-Yi,Liu, Yi-Wei,Lee, Chin-Fa
supporting information, p. 11374 - 11377 (2014/11/08)
A DTBP-promoted metal-free and solvent-free formation of C-Se and C-S bonds through sp3 C-H functionalization of methyl arenes with diselenides and disulfides is described. the Partner Organisations 2014.
Zn in ionic liquid: An efficient reaction media for the synthesis of diorganyl chalcogenides and chalcogenoesters
Narayanaperumal, Senthil,Alberto, Eduardo E.,Gul, Kashif,Kawasoko, Cristiane Yuriko,Dornelles, Luciano,Rodrigues, Oscar E.D.,Braga, Antonio Luiz
experimental part, p. 4723 - 4730 (2011/06/27)
A straightforward and efficient methodology is described to synthesize structurally diverse diorganyl selenides, sulfides, seleno- and thioesters by using commercially available Zn dust in ionic liquid. Excellent yields were achieved under neutral conditions at room temperature in a short time. The solvent/ionic liquid is reusable and exhibited higher performance as compared with organic solvents.
Bimetallic system for the synthesis of diorganyl selenides and sulfides, chiral β-seleno amines, and seleno- and thioesters
Gul, Kashif,Narayanaperumal, Senthil,Dornelles, Luciano,Rodrigues, Oscar E.D.,Braga, Antonio Luiz
supporting information; experimental part, p. 3592 - 3596 (2011/07/31)
The bimetallic reagent Sn(II)/Cu(II) in [bmim]BF4 was efficiently used for the cleavage of diaryl diselenides and disulfides and reacts with a variety of organic substrates, such as organic halides, acid chlorides, and β-amino mesylates affording the diorganyl selenides and sulfides within very short reaction times, under mild conditions and with excellent yields, using BMIM-BF4 as a reusable solvent.
Synthesis of diorganyl selenides mediated by zinc in ionic liquid
Narayanaperumal, Senthil,Alberto, Eduardo E.,Gul, Kashif,Rodrigues, Oscar E. D.,Braga, Antonio L.
supporting information; experimental part, p. 3886 - 3889 (2010/07/05)
Figure presented A new approach for the synthesis of diorganyl selenides is described. By using economically attractive zinc dust in BMIM-BF4, a series of diorganyl selenides were efficiently achieved in excellent yields, under neutral reaction conditions. Compared to the usual organic solvents, BMIM-BF4 exhibited higher performance with the advantage to be reused up to five successive runs.
Ionic liquid: An efficient and recyclable medium for synthesis of unsymmetrical diorganyl selenides promoted by InI
Narayanaperumal, Senthil,Alberto, Eduardo E.,De Andrade, Fabiano Molinos,Lenardao, Eder J.,Taube, Paulo S.,Braga, Antonio L.
experimental part, p. 4647 - 4650 (2009/12/08)
In an environmentally friendly protocol, InI was used as a reducing agent for the Se-Se bond to prepare unsymmetrical diorganyl selenides with very short reaction times, mild conditions and excellent yields using (bmim)BF4 as a recyclable solvent.
Direct conversion of a benzylic hydroxy group into a selenenyl group using the phenyl trimethylsilyl selenide-aluminum bromide combination
Abe, Hitoshi,Yamasaki, Akira,Harayama, Takashi
, p. 1311 - 1313 (2007/10/03)
A new reagent system, phenyl trimethylsilyl selenide-aluminum bromide, was developed for the direct conversion of various benzylic hydroxy groups into a selenenyl group. Treatment of cinnamyl alcohol with this reagent system yielded 3,4-dihydro-4-phenyl-2H-1-benzoselenin via a [3,3]-sigmatropic rearrangement of the intermediate cinnamyl phenyl selenide.
Convenient transformation of benzyl alcohol into its corresponding selenide using the selenolate anion-aluminum chloride combination system
Abe, Hitoshi,Yamasaki, Akira,Fujii, Hiroyuki,Harayama, Takashi
, p. 2223 - 2226 (2007/10/03)
Treatment of benzyl alcohol with a new reagent system, benzene- or methaneselenolate anion-aluminum chloride, yielded the corresponding selenide. The one-pot conversion of benzaldehyde into benzyl selenide was also achieved by this system.
