52693-61-5Relevant academic research and scientific papers
Cobalt Single-Atom-Intercalated Molybdenum Disulfide for Sulfide Oxidation with Exceptional Chemoselectivity
Chen, Zhongxin,Liu, Cuibo,Liu, Jia,Li, Jing,Xi, Shibo,Chi, Xiao,Xu, Haisen,Park, In-Hyeok,Peng, Xinwen,Li, Xing,Yu, Wei,Liu, Xiaowang,Zhong, Linxin,Leng, Kai,Huang, Wei,Koh, Ming Joo,Loh, Kian Ping
, (2019/12/03)
The identification of chemoselective oxidation process en route to fine chemicals and specialty chemicals is a long-standing pursuit in chemical synthesis. A vertically structured, cobalt single atom-intercalated molybdenum disulfide catalyst (Co1-in-MoS2) is developed for the chemoselective transformation of sulfides to sulfone derivatives. The single-atom encapsulation alters the electron structure of catalyst owing to confinement effect and strong metal–substrate interaction, thus enhancing adsorption of sulfides and chemoselective oxidation at the edge sites of MoS2 to achieve excellent yields of up to 99% for 34 examples. The synthetic scopes can be extended to sulfide-bearing alkenes, alkynes, aldehydes, ketones, boronic esters, and amines derivatives as a toolbox for the synthesis of high-value, multifunctional sulfones and late-stage functionalization of pharmaceuticals, e.g., Tamiflu. The synthetic utility of cobalt single atom-intercalated MoS2, together with its reusability, scalability, and simplified purification process, renders it promising for industrial productions.
A Class of Amide Ligands Enable Cu-Catalyzed Coupling of (Hetero)aryl Halides with Sulfinic Acid Salts under Mild Conditions
Zhao, Jinlong,Niu, Songtao,Jiang, Xi,Jiang, Yongwen,Zhang, Xiaojing,Sun, Tiemin,Ma, Dawei
, p. 6589 - 6599 (2018/05/31)
The amide derived from 4-hydroxy-l-proline and 2,6-dimethylaniline is a powerful ligand for Cu-catalyzed coupling of (hetero)aryl halides with sulfinic acid salts, allowing the formation of a wide range of (hetero)aryl sulfones from the corresponding (hetero)aryl halides at considerably low catalytic loadings. The coupling of (hetero)aryl iodides and sodium methanesulfinate proceeds at room temperature with only 0.5 mol % CuI and ligand, representing the first example for Cu-catalyzed arylation at both low catalytic loading and room temperature.
Palladium-catalyzed sulfination of aryl and heteroaryl halides: Direct access to sulfones and sulfonamides
Shavnya, Andrei,Coffey, Steven B.,Smith, Aaron C.,Mascitti, Vincent
supporting information, p. 6226 - 6229 (2014/01/17)
A novel palladium-catalyzed sulfination of aryl and heteroaryl halides is described. This reaction operates under mild conditions and provides access to a wide range of aryl and heteroaryl sulfinates, a useful and versatile class of synthetic intermediates. Capitalizing on this sulfination reaction, one-pot protocols allowing direct access to sulfones and sulfonamides have also been developed. The practicality of these transformations is illustrated with the parallel synthesis of analogues of the drug Viagra.
Enzymatic synthesis of novel chiral sulfoxides employing Baeyer-villiger monooxygenases
Rioz-Martinez, Ana,De Gonzalo, Gonzalo,Pazmino, Daniel E. Torres,Fraaije, Marco W.,Gotor, Vicente
experimental part, p. 6409 - 6416 (2011/02/24)
Optically active sulfoxides are compounds of high interest in organic chemistry. Herein, we report the preparation of a set of chiral heteroaryl alkyl, cyclohexyl alkyl, and alkyl alkyl sulfoxides by using enantioselective sulfoxidation reactions employing three Baeyer-Villiger monooxygenases (BVMOs). Careful selection of the reaction conditions, starting sulfide, and biocatalyst can be used to achieve good to excellent enantiomeric excess values. Thus, valuable chiral synthons can be obtained by performing the reactions under mild and environmentally friendly conditions. The most promising biotransformations that employ a BVMO cell-free extract preparation have been developed on a 250-mg scale to give the chiral sulfoxides in high yields in most of the reactions. Copyright
Synthesis of aryl sulfones via L-proline-promoted CuI-catalyzed coupling reaction of aryl halides with sulfinic acid salts
Zhu, Wei,Ma, Dawei
, p. 2696 - 2700 (2007/10/03)
(Chemical Equation Presented) The CuI/L-proline sodium salt catalyzed coupling reaction of aryl halides with sulfinic acid salts readily occurs at 80-95°C in DMSO to give the corresponding aryl sulfones in good to excellent yields. This process is well-tolerated by a wide range of functional groups including hydroxyl, amino, acetanilide, ketone, ester, and nitrile. Using this method, 4-phenylsulfonyl- and 4-methanesulfonyl-substituted L-phenylalanine derivatives are prepared.
A mild and efficient new synthesis of aryl sulfones from boronic acids and sulfinic acid salts
Beaulieu, Christian,Guay, Daniel,Wang, Zhaoyin,Evans, David A.
, p. 3233 - 3236 (2007/10/03)
A new efficient and mild preparation of sulfones from boronic acids and sulfinic acid salts is reported. The cross-coupling reaction mediated by cupric acetate gives access to a variety of sulfones in excellent yield.
Azetidine derivatives, their preparation and pharmaceutical compositions containing them
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, (2008/06/13)
Compounds of formula: in which R represents a CR1R2, C═C(R5)SO2R6 or C═C(R7)SO2alk radical, their preparation and the pharmaceutical compositions containing them.
SYNTHESIS AND BEHAVIOUR OF NADH MODELS BEARING A CHIRAL SULFOXIDE
Boussad, N.,Trefouel, T.,Dupas, G.,Bourguignon, J.,Queguiner, G.
, p. 127 - 138 (2007/10/02)
Chiral 3-sulfinyl-1,4-dihydropyridine derivatives were synthesized by asymmetric oxidation of the parent 3-pyridine sulfides with Kagan's reagent (Ti(OiPr)4/diethyl tartrate/H2O/tBuOOH = 1/2/1/1).The chemoselective oxidation conditions of the sulfur atom were optimized.One chiral NADH mimic reagent so obtained was used in the reduction of prochiral α,α',α''-trifluoroacetophenone.During this reduction a side reaction occurred i.e. desulfenylation of the reagent.The by-product was identified after trapping with methyl propiolate.This side reaction did not occur in the quinoline series.
