60349-76-0Relevant academic research and scientific papers
Metal- and additive-free oxygen-atom transfer reaction: an efficient and chemoselective oxidation of sulfides to sulfoxides with cyclic diacyl peroxides
Gan, Shaoyan,Yin, Junjie,Yao, Yuan,Liu, Yang,Chang, Denghu,Zhu, Dan,Shi, Lei
supporting information, p. 2647 - 2654 (2017/04/03)
Metal- and additive-free oxidation of a series of sulfides/thioketones has been achieved using cyclic diacyl peroxides as mild oxygen sources. This protocol features simple manipulation, high chemo- and diastereoselectivity, and a broad substrate scope (up to 42 examples), tolerates many common functional groups, and is scalable and applicable to the late-stage sulfoxidation strategy. A preliminary mechanistic study by quantum mechanical calculations suggests that a single two-electron transfer process is energetically more favorable, and indicates the reactivity of cyclic diacyl peroxides distinct from conventional acyclic acyl peroxides.
Polyoxomolybdate-Calix[4]arene Hybrid: A Catalyst for Sulfoxidation Reactions with Hydrogen Peroxide
Meninno, Sara,Parrella, Alessandro,Brancatelli, Giovanna,Geremia, Silvano,Gaeta, Carmine,Talotta, Carmen,Neri, Placido,Lattanzi, Alessandra
supporting information, p. 5100 - 5103 (2015/11/03)
An easily accessible polyoxomolybdate-calix[4]arene hybrid 1 has been synthesized and applied as a heterogeneous catalyst in the sulfoxidation of thioethers to sulfoxides and to sulfones under strictly stoichiometric amounts of 30% H2O2 in CH3CN as the solvent. This study represents the first promising example of successful employment of calixarenes-polyoxometalate (POM) hybrid materials in the area of catalytic oxidations.
Chiral phosphoric acid-catalyzed asymmetric oxidation of aryl alkyl sulfides and aldehyde-derived 1,3-dithianes: Using aqueous hydrogen peroxide as the terminal oxidant
Liu, Zhao-Min,Zhao, Hua,Li, Mei-Qiu,Lan, Yu-Bao,Yao, Qi-Bo,Tao, Jing-Chao,Wang, Xing-Wang
supporting information; experimental part, p. 1012 - 1022 (2012/05/20)
(R)-1,1'-Binaphthyl-2,2'-diol (R-BINOL) derived chiral phosphoric acids have been explored as organocatalysts for the asymmetric oxidation of a series of aryl alkyl sulfides and 1,3-dithianes derived from aldehydes with aqueous hydrogen peroxide (H2O2) as the terminal oxidant. The enantiomerically enriched sulfoxides are obtained in moderate to excellent yield (up to 99%) with excellent diastereoselectivity (up to >99:1 dr) and moderate to good enantioselectivity (up to 91:9 er). In particular, the present protocol stereoselectively provides an efficient access to enantiomerically enriched aryl alkyl sulfoxides and dithioacetal mono-sulfoxides, which strictly restrains the formation of the undesirable by-products: sulfones or disulfoxides. The tracking experiments also verify that this approach proceeds via a direct sulfoxidation process, instead of a kinetic resolution route by overoxidation of the resulting sulfoxides. Copyright
Enantioselective vanadium-catalyzed oxidation of 1,3-dithianes from aldehydes and ketones using β-amino alcohol derived schiff base ligands
Wu, Yinuo,Mao, Fei,Meng, Fanchao,Li, Xingshu
supporting information; experimental part, p. 1707 - 1712 (2011/10/01)
The asymmetric vanadium-catalyzed oxidation of 1,3-dithianes from aldehydes and ketones by β-amino alcohol-derived Schiff base ligands with two stereogenic centers was investigated. Using aqueous hydrogen peroxide as the oxidant and the Schiff base 3b as
An efficient solvent free catalytic oxidation of sulfides to sulfoxides with hydrogen peroxide catalyzed by a binaphthyl-bridged Schiff base titanium complex
De Rosa, Margherita,Lamberti, Marina,Pellecchia, Claudio,Scettri, Arrigo,Villano, Rosaria,Soriente, Annunziata
, p. 7233 - 7235 (2007/10/03)
A titanium binaphthyl-bridged Schiff base complex proved to be an efficient catalyst for the hydrogen peroxide oxidation of aromatic and aliphatic sulfides to the corresponding sulfoxides in satisfactory yields under solvent-free conditions.
Titanocene dichloride as a convenient catalyst for the diastereoselective oxidation of 2-substituted 1,3-dithianes and 1,3-dithiolanes
Della Sala, Giorgio,Labano, Stefania,Lattanzi, Alessandra,Tedesco, Consiglia,Scettri, Arrigo
, p. 505 - 510 (2007/10/03)
Cp2TiCl2 is an efficient catalyst for the diastereoselective mono-oxidation of 2-substituted 1,3-dithianes and 1,3-dithiolanes by tert-butyl hydroperoxide; comparable stereoselectivities and better yields than Ti(i-PrO)4 w
Substituted N-Salicylidene β-Amino Alcohols. Preparation and Use as Chiral Ligands in Enantioselective Sulfoxidation and Conjugate Addition
Skarzewski, Jacek,Ostrycharz, Elzbieta,Siedlecka, Renata,Zielinska-Blajet, Mariola,Pisarski, Bartlomiej
, p. 743 - 757 (2007/10/03)
A high-yielding synthesis of optically active 3,5-disubstituted N-salicylidene β-amino alcohols 6, versatile chiral ligands, is developed. The catalytic use of D or L-N-(3-phenyl-5-nitrosalicylidene)valinol (6j) in enantioselective sulfoxidation reactions (H2O2/VO(acac)2) gives up to 95 percent e.e. The asymmetric conjugate addition of thiophenol to 2-cyclohexen-1-one catalyzed by Ti(OPr-i)4 and 6 leads to maximum of 31 percent e.e.
Vanadium catalyzed enantioselective oxidation of sulfides: Easy transformation of bis(arylthio)alkanes into C2 symmetric chiral sulfoxides
Skarzewski, Jacek,Ostrycharz, Elzbieta,Siedlecka, Renata
, p. 3457 - 3461 (2007/10/03)
A facile and selective method for the title transformation is described. The two-phase oxidation of bis-sulfides with hydrogen peroxide catalyzed by vanadium complex of chiral Schiff base leads to the corresponding chiral mono- and bis-sulfoxides. In the
Asymmetric oxidation of dithioacetals and dithioketals catalyzed by a chiral vanadium complex
Bolm, Garsten,Bienewald, Frank
, p. 1327 - 1328 (2007/10/03)
Vanadium-catalyzed enantioselective oxidations of dithioacetals and dithioketals with 30% aqueous H2O2 give the corresponding monosulfoxides with enantioselectivities of up to 85% ee. The scope of this asymmetric catalysis has been i
Enantioselective preparation of 2-substituted-1,3-dithiane 1-oxides using modified Sharpless sulphoxidation procedures
Page, Philip C. Bulman,Wilkes, Robin D.,Namwindwa, Ernest S.,Witty, Michael J.
, p. 2125 - 2154 (2007/10/03)
Enantioselective sulphoxidation of a wide range of 2-substituted-1,3-diathianes has been carried out using modified Sharpless conditions to furnish the corresponding sulphoxides in optically enriched form. Deacylation of 2-acyl-1,3-dithiane 1-oxide deriva
