58948-52-0Relevant academic research and scientific papers
Laser photolysis studies of endoergonic triplet energy transfer in solution by observing the carbon-sulfur bond cleavage of triplet-sensitized naphthylmethyl phenyl sulfide
Yamaji, Minoru,Wakabayashi, Sayaka,Ueda, Shin-Ichi,Shizuka, Haruo,Tobita, Seiji
, p. 41 - 48 (2003)
A bimolecular rate constant (kq) and an efficiency (αTET) of an endoergonic triplet energy transfer from triplet α-naphthyl phenyl ketone (NPK) to α-naphthylmethyl phenyl sulfide (NMPS) in solution, where the energy difference (ΔET) is 1:7 kcal mol-1, have been determined by means of nanosecond laser flash photolysis. Base on the Arrhenius plots of the kq value for the NPK-NMPS system, an activation energy (ΔEa) for the endoergonic triplet energy transfer is found to be 2.6 kcal mol-1, which is larger than the endothermic energy gap (ΔET = 1.7 kcal mol-1). The endoergonic triplet energy transfer in solution is demonstrated to proceed with the aid of thermal activation for the first time.
Transition-metal-free decarboxylative thiolation of stable aliphatic carboxylates
Xing, Wei-Long,Liu, De-Guang,Fu, Ming-Chen
, p. 4593 - 4597 (2021/02/03)
A transition-metal-free decarboxylative thiolation protocol is reported in which primary, secondary, tertiary (hetero)aryl acetates and α-CN substituted acetates undergo the decarboxylative thiolation smoothly, to deliver a variety of functionalized aryl alkyl sulfides in moderate to excellent yields. Aryl diselenides are also amenable substrates for construction of C-Se bonds under the simple and mild reaction conditions. Moreover, the protocol is successfully applied to the late-stage modification of pharmaceutical carboxylates with satisfactory chemoselectivity and functional-group compatibility. This journal is
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
Alkyl Sulfides as Promising Sulfur Sources: Metal-Free Synthesis of Aryl Alkyl Sulfides and Dialkyl Sulfides by Transalkylation of Simple Sulfides with Alkyl Halides
Liu, Ting,Qiu, Renhua,Zhu, Longzhi,Yin, Shuang-Feng,Au, Chak-Tong,Kambe, Nobuaki
supporting information, p. 3833 - 3837 (2018/12/05)
A site-selective metal-free dealkylative approach to synthesize aryl alkyl and symmetrical dialkyl sulfides has been developed. This procedure is convenient and has wide functional group tolerance giving rise to sulfides carrying various alkyl chains from simple alkyl sulfides and alkyl halides in good to excellent yields. This transalkylation proceeds by an ionic mechanism via sulfonium intermediates and it was proposed that dimethylacetamide (DMAC) may participate in part to promote the reaction.
Preparation method and application of novel ionic binuclear Schiff base titanium complex
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Paragraph 0096; 0097, (2018/04/03)
The invention provides a preparation method of a novel ionic binuclear Schiff base titanium complex and a synthetic method of applying the novel ionic binuclear Schiff base titanium complex to catalyze zinc powder and reduce disulfide or selenide to prepare sulfo(seleno) ester and dissymmetric sulfoether(selenide). The complex is a cationic binuclear Schiff base titanium complex, wherein titaniumatoms are bridged by oxygen atoms and are coordinated with a Schiff base ligand and a hydrone, and an ionic bond is formed by a cation part and an anion part of whole Schiff base titanium. The ionic binuclear Schiff base titanium complex is used as a catalyst, the zinc powder is used as a reducer, the disulfide(selenide) can be reduced and fractured, and the disulfide(selenide) can further and respectively react with anhydride, an alpha-bromo carbonyl compound and bromoalkane to prepare the sulfo(seleno) ester and the dissymmetric sulfoether(selenide). According to the preparation method provided by the invention, the defects that traditional lewis acid halide is deliquescent, an absolute solvent is used, conditions are strict and the like are overcome; an effective path for reducing the disulfide or selenide to prepare the sulfo(seleno) ester and the dissymmetric sulfoether(selenide) is provided, and the preparation method has the advantages of high yield, simpleness in operation andthe like.
Mesolysis Mechanisms of Aromatic Thioether Radical Anions Studied by Pulse Radiolysis and DFT Calculations
Yamaji, Minoru,Tojo, Sachiko,Fujitsuka, Mamoru,Sugimoto, Akira,Majima, Tetsuro
, p. 7890 - 7895 (2015/09/01)
The mesolysis mechanisms for eight aromatic thioether radical anions (ArCH2SAr′?-) generated during radiolysis in 2-methyltetrahydrofuran were studied by spectroscopic measurements and DFT calculation. Seven of ArCH2SAr′s
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.
Iodine-mediated thioetherification of alcohols with disulfides or NaSh under microwave irradiation
Hu, Bolun,Sun, Leilei,Tang, Riyuan,Hu, Huanan
, p. 2556 - 2562,7 (2020/09/16)
An efficient and novel method for the thioetherification of an alcohol with disulfides or NaSH under microwave irradiation is presented. In the presence of iodine, a variety of alcohols were smoothly S-alkylated with disulfides or NaSH to give the corresponding thioethers in moderate to excellent yields. Copyright
Ionic liquid/PPh3 promoted cleavage of diphenyl disulfide and diselenide: A straight-forward metal-free one-pot route to the synthesis of unsymmetrical sulfides and selenides
Banerjee, Subhash,Adak, Laksmikanta,Ranu, Brindaban C.
supporting information; experimental part, p. 2149 - 2152 (2012/05/05)
A metal-free cleavage of diphenyl disulfide and diphenyl diselenide has been achieved using ionic liquid/triphenyl phosphine (PPh3) and a convenient protocol for the one-pot synthesis of unsymmetrical sulfides and selenides by condensing 'in situ' generated thiolate or selenate anion with alkyl halides has been developed. In addition, 1,4-conjugate addition of the generated thiolate anions to activated alkenes has also been demonstrated. The ionic liquid, 1-methyl-3-pentyl imidazolium bromide, [pmIm]Br plays a crucial role in promoting the course of the reactions and shows superior activity and selectivity compared to other solvents. The [pmIm]Br has been reused for at least five times without appreciable loss of activity.
Selective reduction of thioacetal to sulfide by gallium(II) chloride
Ikeshita, Kei-Ichiro,Kihara, Nobuhiro,Ogawa, Akiya
, p. 8773 - 8775 (2007/10/03)
The reaction of dithioacetals with gallium(II) chloride followed by the acid treatment afforded sulfides in good yields.
