- Metal- and additive-free oxygen-atom transfer reaction: an efficient and chemoselective oxidation of sulfides to sulfoxides with cyclic diacyl peroxides
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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.
- Gan, Shaoyan,Yin, Junjie,Yao, Yuan,Liu, Yang,Chang, Denghu,Zhu, Dan,Shi, Lei
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supporting information
p. 2647 - 2654
(2017/04/03)
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- Polyoxomolybdate-Calix[4]arene Hybrid: A Catalyst for Sulfoxidation Reactions with Hydrogen Peroxide
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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.
- Meninno, Sara,Parrella, Alessandro,Brancatelli, Giovanna,Geremia, Silvano,Gaeta, Carmine,Talotta, Carmen,Neri, Placido,Lattanzi, Alessandra
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supporting information
p. 5100 - 5103
(2015/11/03)
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- Chiral phosphoric acid-catalyzed asymmetric oxidation of aryl alkyl sulfides and aldehyde-derived 1,3-dithianes: Using aqueous hydrogen peroxide as the terminal oxidant
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(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
- Liu, Zhao-Min,Zhao, Hua,Li, Mei-Qiu,Lan, Yu-Bao,Yao, Qi-Bo,Tao, Jing-Chao,Wang, Xing-Wang
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supporting information; experimental part
p. 1012 - 1022
(2012/05/20)
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- Enantioselective vanadium-catalyzed oxidation of 1,3-dithianes from aldehydes and ketones using β-amino alcohol derived schiff base ligands
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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
- Wu, Yinuo,Mao, Fei,Meng, Fanchao,Li, Xingshu
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supporting information; experimental part
p. 1707 - 1712
(2011/10/01)
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- An efficient solvent free catalytic oxidation of sulfides to sulfoxides with hydrogen peroxide catalyzed by a binaphthyl-bridged Schiff base titanium complex
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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.
- De Rosa, Margherita,Lamberti, Marina,Pellecchia, Claudio,Scettri, Arrigo,Villano, Rosaria,Soriente, Annunziata
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p. 7233 - 7235
(2007/10/03)
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- Titanocene dichloride as a convenient catalyst for the diastereoselective oxidation of 2-substituted 1,3-dithianes and 1,3-dithiolanes
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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
- Della Sala, Giorgio,Labano, Stefania,Lattanzi, Alessandra,Tedesco, Consiglia,Scettri, Arrigo
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p. 505 - 510
(2007/10/03)
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- Substituted N-Salicylidene β-Amino Alcohols. Preparation and Use as Chiral Ligands in Enantioselective Sulfoxidation and Conjugate Addition
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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.
- Skarzewski, Jacek,Ostrycharz, Elzbieta,Siedlecka, Renata,Zielinska-Blajet, Mariola,Pisarski, Bartlomiej
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p. 743 - 757
(2007/10/03)
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- Vanadium catalyzed enantioselective oxidation of sulfides: Easy transformation of bis(arylthio)alkanes into C2 symmetric chiral sulfoxides
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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
- Skarzewski, Jacek,Ostrycharz, Elzbieta,Siedlecka, Renata
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p. 3457 - 3461
(2007/10/03)
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- Asymmetric oxidation of dithioacetals and dithioketals catalyzed by a chiral vanadium complex
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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
- Bolm, Garsten,Bienewald, Frank
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p. 1327 - 1328
(2007/10/03)
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- Enantioselective preparation of 2-substituted-1,3-dithiane 1-oxides using modified Sharpless sulphoxidation procedures
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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
- Page, Philip C. Bulman,Wilkes, Robin D.,Namwindwa, Ernest S.,Witty, Michael J.
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p. 2125 - 2154
(2007/10/03)
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- The Synthesis and Pyrolysis of 2-Substituted 1,3-Dithiane 1,1-Dioxide
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The 2-substituted derivatives of tetrahydrothiophene were obtained by pyrolysis of monosulfones of 1,3-dithiane, the latter being synthesized in a three-step procedure.
- Kabzinska, Krystyna,Kawecki, Robert
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p. 117 - 121
(2007/10/02)
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