13153-10-1Relevant articles and documents
Ionic liquid-functionalized amphiphilic Janus nanosheets afford highly accessible interface for asymmetric catalysis in water
Li, Chaoping,Liu, Su,Pi, Yibing,Feng, Jingwen,Liu, Zewei,Li, Shiye,Tan, Rong
, p. 236 - 245 (2021)
High oil/water interfacial area together with accessible interfaces for regents is the key to achieving efficient asymmetric catalysis in water. Herein, by taking advantage of the excellent interfacial activity of Janus nanosheets (JNS), as well as the unique compatibility of imidazolium ionic liquid (IL), we developed a series of IL-functionalized amphiphilic Janus mesosilica nanosheets which afford highly accessible reaction interfaces for highly enantioselective sulfoxidation in water. The JNS-typed chiral salen TiIV catalysts were prepared by selectively decorating hydrophobic chiral salen TiIV complex on one side of Janus mesosilica nanosheets through the imidazolium-based IL linker. Benefiting from the two-dimensional porous Janus structure, as well as the compatible IL linker, the IL-tagged JNS catalysts afforded high oil/water interfacial areas and highly accessible reaction interface for sulfides and H2O2, significantly accelerating asymmetric sulfoxidation in water using H2O2 as an oxidant. In addition, they can be facilely recovered for stable reuse by simple centrifugation.
The Pummerer-type reaction mediated ring-opening of 2-alkyl substituted 1-[(2-methoxyethoxy)methoxy]-2-(phenylsulfinyl)cyclopropanes
Pohmakotr, Manat,Moosophon, Panawan,Pisutjaroenpong, Somchai,Tuchinda, Patoomratana,Reutrakul, Vichai
, p. 4389 - 4391 (2001)
α-Lithiated 1-[(2-methoxyethoxy)methoxy]-2-(phenylsylfinyl)cyclopropane reacted smoothly with alkylating agents to afford the corresponding α-alkylated cyclopropylsulfoxides, which underwent the Pummerer-type reaction mediated ring-opening at low temperature (-78°C) by employing TFAA/Pri2NEt/CH2Cl2 to give mixtures of β-(phenylthio)-α,β- and γ,δ-unsaturated aldehydes.
Oxidation of organic sulfides with clay-supported iodosylbenzene as oxygen donor
Kannan, Pothiraj,Sevvel, Ranganathan,Rajagopal, Seenivasan,Pitchumani, Kasi,Srinivasan, Chockalingam
, p. 7635 - 7640 (1997)
Alkyl, aryl and diaryl sulfides afford excellent yields of sulfoxides with PhIO supported on natural (montmorillonite, KSF and bentonite clay) as well as cation-exchanged clays of K10-montmorillonite in acetonitrile suspension and also in solid state. A l
Light-controlled cooperative catalysis of asymmetric sulfoxidation based on azobenzene-bridged chiral salen TiIVcatalysts
Fu, Wenqin,Gao, Mengqiao,Li, Chaoping,Pi, Yibing,Tan, Rong,Wang, Weiying,Yin, Donghong
, p. 5993 - 5996 (2020)
Incorporation of azobenzene into the linker of bimetallic chiral salen TiIVcatalysts allowed the photoswitchable arrangement of the two Ti(salen) units throughcis/transphotoisomerization of azobenzene. The differently arranged Ti(salen) units changed their cooperative function to reflect the positional relationships, as a result, their efficiency as cooperative catalysts in asymmetric sulfoxidation could be readily controlled by light stimuli.
Efficient and convenient oxidation of sulfides to sulfoxides with molecular oxygen catalyzed by Mn(OAc)2 in ionic liquid [C12mim][NO3]
Hu, Yu-Lin,Fang, Dong,Xing, Rong
, p. 51140 - 51145 (2004)
A simple, efficient, and eco-friendly procedure for aerobic oxidation of sulfides catalyzed by Mn(OAc)2/[C12mim][NO3] has been developed. The reactions afford the target products in good to high yields and no over-oxidatio
Biocatalytic Oxidation of Sulfides to Sulfones
Dhiman, Shefali
, p. 250 - 255 (2021/03/29)
This paper describes a method for the biocatalytic oxidation of sulfides. During the screening of microorganisms using pure cultures of bacteria and fungi for the oxidation of sulfides, it was observed that a number of strains of microorganisms, were able to oxidize various sulfides (1-4), but the desired sulfoxide was either not obtained or obtained only as a minor product. A close observation of the reaction showed complete oxidation and thus sulfone (5-8) formation had occurred in these cases. Sulfones are used to stabilize intermediates like α-radicals, α-anions etc. and also used as cationic synthons in many known reactions. This prompted us to explore the sulfone synthesis by biocatalytic route. Approximately 20% of the strains tested (400 bacterial and 200 fungal) showed the formation of sulfone with conversion rate varying from 3 to 100% based on TLC analysis. There were two strains of fungi, Aspergillus ochraceus MTCC 5245 and Penicillium Funiculosum MTCC 5246 which showed excellent biocatalytic activity for oxidation sulfides to corresponding sulfones in high yield. In all these strains, the product was different from corresponding standard sulfoxide prepared by oxidation with m-chloroperbenzoic acid but well corresponded with the standard sample of sulfone prepared by oxidation of the corresponding sulfides with oxone. The identity of sulfones in all cases was confirmed by 1H NMR. Published by Oriental Scientific Publishing Company
An ionic liquid-functionalized amphiphilic Janus material as a Pickering interfacial catalyst for asymmetric sulfoxidation in water
Zhang, Mingjie,Tang, Zhiyang,Fu, Wenqin,Wang, Weiying,Tan, Rong,Yin, Donghong
supporting information, p. 592 - 595 (2019/02/05)
Ionic liquid-functionalized amphiphilic Janus chiral salen TiIV catalysts were prepared by partial hydrophobic modification of silica with a chiral salen TiIV complex through an imidazolium ionic liquid (IL) linker. By optimizing their hydrophobic/hydrophilic balance, the IL-functionalized JNP materials exhibited excellent interfacial activity, significantly accelerating asymmetric sulfoxidation in water through the formation of stable Pickering emulsions. Moreover, catalyst recovery was readily achieved using centrifugation.
