125877-23-8Relevant academic research and scientific papers
Heterogeneously Ni-Pd nanoparticle-catalyzed base-free formal C-S bond metathesis of thiols
Mitamura, Kanju,Yatabe, Takafumi,Yamamoto, Kidai,Yabe, Tomohiro,Suzuki, Kosuke,Yamaguchi, Kazuya
supporting information, p. 3749 - 3752 (2021/04/21)
This study rationally designed a heterogeneously catalyzed system (i.e., using Ni-Pd alloy nanoparticles supported on hydroxyapatite (Ni-Pd/HAP) under an H2atmosphere) achieving an efficient base-free formal C-S bond metathesis of various thiolsviasuppression of the Ni catalysis deactivation.
Copper-Catalyzed Production of Diaryl Sulfides Using Aryl Iodides and a Disilathiane
Ogiwara, Yohei,Maeda, Hiromu,Sakai, Norio
supporting information, p. 655 - 657 (2017/11/29)
A disilathiane was found to be a novel S1 source for the copper-catalyzed synthesis of diaryl sulfides using aryl iodides. The reaction of iodoarenes and hexamethyldisilathiane, (Me 3 Si) 2 S, in the presence of a catalytic amount of CuI/1,10-phenanthroline provided various types of diaryl sulfides in good yields.
Palladium-Catalyzed Double Borylation of Diaryl Sulfoxides with Diboron
Saito, Hayate,Nogi, Keisuke,Yorimitsu, Hideki
, p. 4769 - 4774 (2017/09/30)
Borylation of the C-S bond of diaryl sulfoxides with bis(pinacolato)diboron (B 2 pin 2) is accomplished by means of a phosphine-ligated palladium catalyst and LiN(SiMe 3) 2 as a base. Both of the aryl rings of the diaryl sulfoxides are converted into borylated products.
Photoinduced nucleophilic substitution of aryl halides with potassium thioacetate - A one-pot approach to aryl methyl and diaryl sulfides
Schmidt, Luciana C.,Rey, Valentina,Penenory, Alicia B.
, p. 2210 - 2214 (2007/10/03)
Aryl methyl sulfides and diaryl sulfides were prepared by photoinduced reactions of potassium thioacetate with aryl halides under entrainment conditions. Without isolation, the arene thiolates obtained by the aromatic substitution were quenched with methyl iodide to afford the aryl methyl sulfides in 26-59% yields in a "one-pot" procedure together with the diaryl sulfides in variable yields (3-31 %). By optimization of the reaction conditions it was possible to improve the formation of the Ar2S, going from moderate to good yields (64-83%). Wiley-VCH Verlag GmbH & Co. KGaA, 2006.
A mild and highly convenient chemoselective alkylation of thiols using Cs2CO3-TBAI
Salvatore, Ralph Nicholas,Smith, Robert A.,Nischwitz, Adam K.,Gavin, Terrence
, p. 8931 - 8935 (2007/10/03)
A mild and improved method for the synthesis of thioethers has been developed. In the presence of cesium carbonate, tetrabutylammonium iodide, and DMF, various alkyl and aryl thiols underwent S-alkylation to afford structurally diverse sulfides in high yield. Unprotected mercaptoalcohols and thioamines reacted chemoselectively at the sulfur moiety exclusively. An example of a one-pot, solid-phase synthesis of a thioether is also described.
One-Pot Two-Step Synthesis of Aryl Sulfur Compounds by Photoinduced Reactions of Thiourea Anion with Aryl Halides
Argueello, Juan E.,Schmidt, Luciana C.,Penenory, Alicia B.
, p. 4133 - 4136 (2007/10/03)
(Equation presented) The photoinduced reactions of aryl halides with the thiourea anion afford arene thiolate ions in DMSO. These species without isolation, and by a subsequent aliphatic nucleophilic substitution, S RN1 reaction, oxidation, or protonation, yield aryl methyl sulfides, diaryl sulfides, diaryl disulfides, and aryl thiols with good yields (50-80%). This is a simple and convenient approach which involves the use of the commercially available and inexpensive thiourea in a one-pot two-step process for the synthesis of aromatic sulfur compounds.
Remote Pummerer Reaction via Intermolecular Through-Space Interaction between Sulfonium and Sulfenyl Sulfur Atoms
Kobayashi, Kenji,Koyama, Emiko,Namatame, Kazuhiko,Kitaura, Toyokazu,Kono, Chihiro,Goto, Mariko,Obinata, Takanobu,Furukawa, Naomichi
, p. 3190 - 3195 (2007/10/03)
The remote Pummerer reaction of the mono-sulfoxide of p-bis(methylthio)-aromatic 1 is described. The reaction of 1 with (CF3CO)2O in CH2Cl2 gave a mixture of the corresponding mono-Pummerer product 2, the bis-Pummerer product 3, and the bis-sulfide 4 in an n:1:1 ratio (n ≥ 2). The 1:1 formation of 3 and 4 indicates an intermolecular interaction between sulfur atoms. The reaction with the deuterium-labeled 1-d3 showed that the formation of 2 occurs at the sulfenyl as well as sulfinyl groups in 1a-d3-1d-d3, in which the product ratio of 2-d3:2-d2 is in the range of 3.5-10. On the other hand, the Pummerer reaction of 1e-d3 occurred preferably at the sulfinyl group in a usual manner. The reaction of a 1:1 mixture of the bis-sulfide 4 and the bis-sulfoxide 5 with (CF3-CO)2O also gave 2, 3, and 4 in a ratio similar to that for the reaction of 1. The mechanism in the present remote Pummerer reactions is discussed in light of an intermolecular through-space interaction between the sulfonium and sulfenyl sulfur atoms, and a dithia dication dimer B and/or a bis(dithia dication) cyclic dimer C are proposed as intermediates.
