65151-60-2Relevant academic research and scientific papers
Nanolayered cobalt-molybdenum sulphides (Co-Mo-S) catalyse borrowing hydrogen C-S bond formation reactions of thiols or H2S with alcohols
Corma, Avelino,Sorribes, Iván
, p. 3130 - 3142 (2019/03/13)
Nanolayered cobalt-molybdenum sulphide (Co-Mo-S) materials have been established as excellent catalysts for C-S bond construction. These catalysts allow for the preparation of a broad range of thioethers in good to excellent yields from structurally diverse thiols and readily available primary as well as secondary alcohols. Chemoselectivity in the presence of sensitive groups such as double bonds, nitriles, carboxylic esters and halogens has been demonstrated. It is also shown that the reaction takes place through a hydrogen-autotransfer (borrowing hydrogen) mechanism that involves Co-Mo-S-mediated dehydrogenation and hydrogenation reactions. A novel catalytic protocol based on the thioetherification of alcohols with hydrogen sulphide (H2S) to furnish symmetrical thioethers has also been developed using these earth-abundant metal-based sulphide catalysts.
Synthesis of aryl cyclopropyl sulfides through copper-promoted S-cyclopropylation of thiophenols using cyclopropylboronic acid
Benoit, Emeline,Fnaiche, Ahmed,Gagnon, Alexandre
, p. 1162 - 1171 (2019/06/08)
The copper-promoted S-cyclopropylation of thiophenols using cyclopropylboronic acid is reported. The procedure operates under simple conditions to afford the corresponding aryl cyclopropyl sulfides in moderate to excellent yields. The reaction tolerates substitution in ortho-, meta- and para-substitution as well as electron-donating and electron-withdrawing groups. The S-cyclopropylation of a thiophenol was also accomplished using potassium cyclopropyl trifluoroborate.
Stereoretentive C(sp3)-S Cross-Coupling
Zhu, Feng,Miller, Eric,Zhang, Shuo-Qing,Yi, Duk,O'Neill, Sloane,Hong, Xin,Walczak, Maciej A.
supporting information, p. 18140 - 18150 (2019/01/04)
We report a stereoretentive cross-coupling reaction of configurationally stable nucleophiles with disulfide and N-sulfenylsuccinimide donors promoted by Cu(I). We demonstrate the utility of this method in the synthesis of thioglycosides derived from simple alkyl and aryl thiols, thioglycosides, and in the glycodiversification of cysteine residues in peptides. These reactions operate well with carbohydrate substrates containing common protective groups and reagents with free hydroxyl and secondary amide functionalities under standardized conditions. Competition experiments in combination with computational DFT studies established that the putative anomeric intermediate is an organocopper species that is configurationally stable and resistant to epimerization due to its short lifetime. The subsequent reductive elimination from the Cu(III) intermediate is rapid and stereoretentive. Taken together, the glycosyl cross-coupling is ideally suited for late stage glycodiversification and bioconjugation under highly controlled installation of the aliphatic carbon-sulfur bonds.
Chemoselective synthesis of diaryl disulfides via a visible light-mediated coupling of arenediazonium tetrafluoroborates and CS2
Leng, Jing,Wang, Shi-Meng,Qin, Hua-Li
supporting information, p. 903 - 909 (2017/06/23)
A highly efficient and chemoselective method for the synthesis of diaryl disulfides is developed via a visible light-promoted coupling of readily accessible arenediazonium tetrafluoroborates and CS2. This practical and convenient protocol provides a direct pathway for the assembly of a series of disulfides in an environmentally friendly manner with good to excellent yields.
Disulfide-based metal-free α-sulfanylation of ketones
Vaquer, Andrea F.,Frongia, Angelo,Secci, Francesco,Tuveri, Enrica
, p. 96695 - 96704 (2015/11/24)
An eco-friendly methodology for the direct α-sulfanylation of ketones, has been developed. The procedure, based on the use of functionalized diaryldisulfides and catalyzed by d,l-proline, represents a mild and efficient approach for the preparation of α-arylthio-ketones.
Palladium-catalyzed synthesis of ammonium sulfinates from aryl halides and a sulfur dioxide surrogate: A gas-and reductant-free process
Emmett, Edward J.,Hayter, Barry R.,Willis, Michael C.
, p. 10204 - 10208 (2015/03/31)
Sulfonyl-derived functional groups populate a broad range of useful molecules and materials, and despite a variety of preparative methods being available, processes which introduce the most basic sulfonyl building block, sulfur dioxide, using catalytic methods, are rare. Described herein is a simple reaction system consisting of the sulfur dioxide surrogate DABSO, triethylamine, and a palladium(0) catalyst for effective convertion of a broad range of aryl and heteroaryl halides into the corresponding ammonium sulfinates. Key features of this gas-and reductant-free reaction include the low loadings of palladium (1 mol) and ligand (1.5 mol) which can be employed, and the use of isopropyl alcohol as both a solvent and formal reductant. The ammonium sulfinate products are converted in situ into a variety of sulfonyl-containing functional groups, including sulfones, sulfonyl chlorides, and sulfonamides.
Oxidative coupling of diaryldisulfides by MoCl5 to thianthrenes
Spurg, Anke,Schnakenburg, Gregor,Waldvogel, Siegfried R.
supporting information; experimental part, p. 13313-13317+13274 (2010/06/15)
"Chemical Equation Presented" Oxidative C-S coupling: The oxidative coupling reaction of 1,2-diaryldisulfides by using MoCl5 or mixtures thereof with TiCl4 gives fast and efficient access to dibenzo[b,e] [1,4]dithiins such as that depicted (thianthrenes).
Direct aromatic tert-butylation during the synthesis of thiochroman-4-ones
Clayton, Stephen E.,Gabbutt, Christopher D.,Hepworth, John D.,Mark Heron
, p. 939 - 946 (2007/10/02)
The synthesis of thiochroman-4-ones from thiophenols and 3-methylbut-2-enoic acid effected by methane sulphonic acid is accompanied by tert-butylation of the aromatic ring. 3-Arylthiobutanoic acids, available using β-butyrolactone, are efficiently cyclised in the same manner.
Synthesis of Soluble Poly(thio-2,6-dimethyl-1,4-phenylene) by Oxidative Polymerization of Bis(3,5-dimethylphenyl) Disulfide
Jikei, Mitsutoshi,Katoh, Junya,Sato, Naohiko,Yamamoto, Kimihisa,Nishide, Hiroyuki,Tsuchida, Eishun
, p. 2029 - 2036 (2007/10/02)
Poly(thio-2,6-dimethyl-1,4-phenylene) has been prepared by the oxidative polymerization of bis(3,5-dimethylphenyl) disulfide.The obtained polymer is amorphous and soluble in common organic solvents.The properties of the polymer are similar to those of poly(oxy-2,6-dimethyl-1,6-phenylene), rather than poly(thio-1,4-phenylene) (PPS).The polymer is obtained as a high molecular weight substance compared with other substituted or non-substituted PPS derivatives by the oxidative polymerization.The polymer containing a disulfide bond, whose structure was confirmed by the reduction of the polymer, acts as an initiator of radical polymerization.
A MILD REDUCTION OF ARENESULFONIC ACID AND ITS DERIVATIVES WITH DIPHOSPHOROUS TETRAIODIDE
Suzuki, Hitomi,Tani, Hiroyuki,Osuka, Atsuhiro
, p. 139 - 142 (2007/10/02)
When treated with diphosphorous tetraiodide in boiling acetonitrile or under neat conditions, arenesulfonic acids, their salts, chlorides, esters, and amides are reduced to aryl disulfides in good to moderate yields.
