1887-29-2Relevant articles and documents
Enabling olefin metathesis on proteins: Chemical methods for installation of S-allyl cysteine
Chalker, Justin M.,Lin, Yuya A.,Boutureira, Omar,Davis, Benjamin G.
, p. 3714 - 3716 (2009)
Multiple, complementary methods are reported for the chemical conversion of cysteine to S-allyl cysteine on protein surfaces, a useful transformation for the exploration of olefin metathesis on proteins.
Synthesis of 1,4-dithiins from pentathiepins
Amelichev, Stanislav A.,Konstantinova, Lidia S.,Obruchnikova, Natalia V.,Rakitin, Oleg A.,Rees, Charles W.
, p. 4529 - 4532 (2006)
Fused aromatic and heterocyclic 1,2,3,4,5-pentathiepins react with triphenylphosphine and alkynes bearing electron-withdrawing groups to give the corresponding 1,4-dithiins in high yields. Unsymmetrical alkynes add regioselectively to afford products in agreement with the electron distribution in a proposed reaction intermediate. A mechanism for these reactions is proposed.
Sodium thiosulfonate salts: Molecular and supramolecular structural features and solution radiolytic properties
Fischmann, Adam J.,Spiccia, Leone
, p. 12310 - 12319 (2011)
Three sodium thiosulfonate salts, NaMeS2O2· H2O, NaPhS2O2 and NaMeC6H 4S2O2 have been prepared by the direct reaction of the sodium sulfinate salts with elemental sulfur, a clean, benign route that produces no by-products. The structures of the phenyl (which crystallised as a hydrate, NaPhS2O2·1.5H2O) and p-tolyl compounds were determined by X-ray crystallography. For the p-tolyl derivative, NaMeC6H4S2O2, the unexpected coordination of the pendant sulfur atom was found, a feature not reported previously for thiosulfonate salts, and observed only in two of the more common thiosulfate salts. Intermolecular CH/π interactions are postulated to contribute to the driving force of sulfur coordination, otherwise a different orientation of the aromatic rings would be expected. For NaPhS2O 2·1.5H2O, the water ligands and thiosulfonate anions each contribute three oxygen atoms to form a NaO6 coordination sphere. The thiosulfonate and water oxygens bridge to other sodium atoms forming a three-dimensional layer structure consisting of sheets of NaPhS 2O2·1.5H2O with a hydrophilic interior layer, comprising the sodium ions, water ligands and -S2O 2- groups, and a hydrophobic exterior formed by the phenyl substituent. The structure is further stabilised by an extensive H-bonding network between the ligated water and the non-coordinating thiosulfonate sulfur atom forming part of the hydrophilic layer and by weak intermolecular edge-to-face CH/π interactions between the sheets. Investigation of the radical chemistry of the three salts using pulse radiolysis indicated that oxidation of NaMeS2O2·H2O involves formation of a sulfur-centred radical rather than hydrogen abstraction from the methyl substituent, whereas oxidation of the aromatic ring is the preferred pathway for the phenyl and p-tolyl derivatives.
Synthesis of C- and N-Substituted 1,5,2,6-Dithiadiazocanes –Electrophilic-Nucleophilic Thioamination (ENTA) Reagents
Bagd?iūnas, Gintautas,Javorskis, Tomas,Jurys, Arminas,Orentas, Edvinas
supporting information, p. 3329 - 3335 (2021/07/02)
A synthetic method is presented for S?N bond formation starting from cheap and affordable materials. We show that (un)substituted N-protected cyclic eight-membered C2-symmetric sulfenamides have been prepared in a few steps using this procedure. The synthetic utility of these ambipolar derivatives was demonstrated in a variety of synthetic transformations affording different S,N-heterocyles of pharmaceutical relevance in one or two steps from simple starting materials. (Figure presented.).
Scalable Synthesis of S-Fluoromethyl Benzenesulfonothioate
Chen, Wenbo,Lu, Long,Shen, Qilong,Yao, Ruichao,Zhao, Qunchao
, p. 1090 - 1094 (2020/07/15)
A general and practical method for the preparation of S-fluoromethyl benzenesulfonothioate on a 500 g scale in two steps from readily available CH2FCl, sulfur, and sodium benzenesulfinate is reported. The reaction was found to be rather sensitive to water and temperature. Furthermore, the main side product of the reaction was identified to be S-phenyl benzenesulfonothioate.
Nickel-Catalyzed Defluorinative Reductive Cross-Coupling Reaction of gem-Difluoroalkenes with Thiosulfonate or Selenium Sulfonate
Li, Jian,Rao, Weidong,Wang, Shun-Yi,Ji, Shun-Jun
, p. 11542 - 11552 (2019/09/30)
A nickel-catalyzed defluorinative reductive cross-coupling of gem-difluoroalkenes with thiosulfonate or selenosulfonates is described. The reaction involves the formation of thiolated or selenylated monofluoroolefins via regioselective C-F bond cleavage and C-S or C-Se bond formation and features easily available substrates, mild reaction conditions, and high E-selectivity. One of the derivatives by further cross coupling with PhMgBr exhibited an aggregation-induced emission enhancement effect.
Rh(ii)/phosphine-cocatalyzed synthesis of dithioketal derivatives from diazo compounds through simultaneous construction of two different C-S bonds
Rao, Changqing,Mai, Shaoyu,Song, Qiuling
supporting information, p. 5964 - 5967 (2018/06/18)
Rhodium(ii)/phosphine-cocatalyzed bis-sulfuration of α-diazocarbonyl compounds using thiosulfonates as the sulfenylating agent, which provided two sulfur-containing moieties, was developed via simultaneous inter- and intra-molecular C-S bond formation. This novel protocol provides a rapid synthetic route to dithioketal derivatives in moderate to good yields in an atom-economic process. The transformation is proposed to proceed through phosphine ylide formation followed by S(O2)-S bond cleavage and rearrangement.
Copper-Catalyzed Oxidative Trifunctionalization of Olefins: An Access to Functionalized β-Keto Thiosulfones
Huang, Shuai,Thirupathi, Nuligonda,Tung, Chen-Ho,Xu, Zhenghu
, p. 9449 - 9455 (2018/08/01)
Aerobic oxidative trifunctionalization of olefins for the synthesis of functionalized β-keto thiosulfones has been described. The transformation proceeds through molecular oxygen activation under copper catalysis and forms the two new C-S bonds in a single operation using mild conditions. A novel Cu-catalyzed sulfonyl radical addition/oxidation/funtionalization relay mechanism was proposed for the discovered reaction.
Direct Monofluoromethylthiolation with S-(Fluoromethyl) Benzenesulfonothioate
Zhao, Qunchao,Lu, Long,Shen, Qilong
supporting information, p. 11575 - 11578 (2017/09/11)
An electrophilic shelf-stable monofluoromethylthiolating reagent S-(fluoromethyl) benezenesulfonothioate (1) was developed. In the presence of a copper catalyst, reagent 1 coupled with a variety of aryl boronic acids to give the corresponding monofluoromethylthiolated arenes in high yields. In addition, addition of reagent 1 to alkyl alkenes in the presence of a silver catalyst gave alkyl monofluoromethylthioethers in high yields.
Monofluoromethylthiolation reagent, and preparation method, preparative intermediate and application thereof
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Paragraph 0179; 0180; 0181, (2017/09/05)
The invention discloses a monofluoromethylthiolation reagent, and a preparation method, preparative intermediate and application thereof. Structure of the monofluoromethylthiolation reagent is shown as in formula I that is shown in the description, wherein R1, R2, R3, R4 and R5 are respectively chosen from one or any of H, C1-C6 linear or branched alkyl, C1-C6 linear or branched alkoxy, C1-C6 linear or branched halogenated alkyl, halogen, nitryl, hydroxyl, cyano group and amino independently. Monofluoromethylthio group is introduced into molecules directly, so that compared with indirect introduction methods in the prior art, the method for the monofluoromethylthiolation reagent has the advantages of good safety, high efficiency, low cost, high substrate universality, mild condition and wide application range. The monofluoromethylthiolation reagent successfully realizes bifunctional reaction of inactivated olefin, coupling reaction of arylboronic acid and other reactions, and an important methodology research foundation is provided for medicine, pesticide, material and other fields.
