4336-57-6Relevant academic research and scientific papers
Radical-mediated aerobic oxidation of substituted styrenes and stilbenes
Aman, Hasil,Chiu, Wei-Hua,Chuang, Gary Jing,Liu, Pin-Heng
supporting information, p. 20103 - 20106 (2021/12/02)
A 2,2-azobis(isobutyronitrile)-catalyzed oxidative cleavage of alkenes with molecular oxygen as the oxidant was described. Carbonyl compounds and oxiranes were obtained in moderate yield under mild conditions. This study provided useful insights into the mechanism of aerobic oxidative cleavage of alkenes.
Synthesis of Epoxides from Alkyl Bromides and Alcohols with in Situ Generation of Dimethyl Sulfonium Ylide in DMSO Oxidations
Zhang, Zhi-Wei,Li, Hai-Bo,Li, Jin,Wang, Cui-Cui,Feng, Juan,Yang, Yi-Hua,Liu, Shouxin
, p. 537 - 547 (2020/01/02)
Direct conversion of the readily available alkyl bromides and alcohols to value-added epoxides using dimethyl sulfoxide (DMSO) under mild reaction conditions has been developed. Benzyl and allyl bromides, and activated and unactivated alcohols all proceeded smoothly to give epoxides in high to excellent yield. Dimethyl sulfide, generated by DMSO oxidations, was in situ elaborated to form the substituted dimethyl sulfonium ylide species that participates in the Corey-Chaykovsky epoxidation in a domino and one-pot fashion, respectively.
A mesoporous NNN-pincer-based metal-organic framework scaffold for the preparation of noble-metal-free catalysts
Zhang, Yingmu,Li, Jialuo,Yang, Xinyu,Zhang, Peng,Pang, Jiandong,Li, Bao,Zhou, Hong-Cai
, p. 2023 - 2026 (2019/02/19)
Through topology-guided synthesis, a Zr-based mesoporous MOF was successfully constructed, adopting a β-cristobalite-type structure. The MOF is embedded with well-arranged terpyridine coordination sites for facile post-synthetic metalation, and can be effectively used as a general scaffold for the preparation of noble-metal-free catalysts. For instance, the scaffolded metal@MOF material exhibits highly efficient catalytic activity for alkene epoxidation and arene borylation.
Method used for direct synthesis of epoxy compounds from alcohol
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Paragraph 0196-0203, (2019/10/08)
The invention discloses a method used for direct synthesis of an epoxy compounds from an alcohol. According to the method, an alcohol is taken as a raw material, Swern oxidation is adopted to synthesize an aldehyde, a bromo-hydrocarbon and an alkali are added into the aldehyde directly to construct epoxy functional groups, and generate the epoxy compound. According to the method, one-pot method is adopted to realize direct epoxidation of the alcohol, the synthesis route is simple, the preparation process is easy to control, no catalyst is needed in the process, substrate suitable range is wide, reagents are cheap and easily available, preparation conditions are mild, reaction yield is high, and the method is suitable for synthesis of epoxy compounds.
One-Step Synthesis of Hybrid Core–Shell Metal–Organic Frameworks
Yang, Xinyu,Yuan, Shuai,Zou, Lanfang,Drake, Hannah,Zhang, Yingmu,Qin, Junsheng,Alsalme, Ali,Zhou, Hong-Cai
, p. 3927 - 3932 (2018/03/21)
Epitaxial growth of MOF-on-MOF composite is an evolving research topic in the quest for multifunctional materials. In previously reported methods, the core–shell MOFs were synthesized via a stepwise strategy that involved growing the shell-MOFs on top of the preformed core-MOFs with matched lattice parameters. However, the inconvenient stepwise synthesis and the strict lattice-matching requirement have limited the preparation of core–shell MOFs. Herein, we demonstrate that hybrid core–shell MOFs with mismatching lattices can be synthesized under the guidance of nucleation kinetic analysis. A series of MOF composites with mesoporous core and microporous shell were constructed and characterized by optical microscopy, powder X-ray diffraction, gas sorption measurement, and scanning electron microscopy. Isoreticular expansion of microporous shells and orthogonal modification of the core was realized to produce multifunctional MOF composites, which acted as size selective catalysts for olefin epoxidation with high activity and selectivity.
One-pot synthesis of epoxides from benzyl alcohols and aldehydes
Alfonzo, Edwin,Mendoza, Jesse W.L.,Beeler, Aaron B.
supporting information, p. 2308 - 2312 (2018/09/14)
A one-pot synthesis of epoxides from commercially available benzyl alcohols and aldehydes is described. The reaction proceeds through in situ generation of sulfonium salts from benzyl alcohols and their subsequent deprotonation for use in Corey–Chaykovsky epoxidation of aldehydes. The generality of the method is exemplified by the synthesis of 34 epoxides that were made from an array of electronically and sterically varied alcohols and aldehydes.
Continuous Flow Synthesis and Purification of Aryldiazomethanes through Hydrazone Fragmentation
Lévesque, éric,Laporte, Simon T.,Charette, André B.
, p. 837 - 841 (2017/01/14)
Electron-rich diazo compounds, such as aryldiazomethanes, are powerful reagents for the synthesis of complex structures, but the risks associated with their toxicity and instability often limit their use. Flow chemistry techniques make these issues avoidable, as the hazardous intermediate can be used as it is produced, avoiding accumulation and handling. Unfortunately, the produced stream is often contaminated with other reagents and by-products, making it incompatible with many applications, especially in catalysis. Herein is reported a metal-free continuous flow method for the production of aryldiazomethane solutions in a non-coordinating solvent from easily prepared, bench-stable sulfonylhydrazones. All by-products are removed by an in-line aqueous wash, leaving a clean, base-free diazo stream. Three successful sensitive metal-catalyzed transformations demonstrated the value of the method.
The B(C6F5)3-Catalyzed Tandem Meinwald Rearrangement-Reductive Amination
Tiddens, Martine R.,Klein Gebbink, Robertus J. M.,Otte, Matthias
supporting information, p. 3714 - 3717 (2016/08/16)
A system of three coupled catalytic cycles enabling the one-pot transformation of epoxides to amines via Meinwald rearrangement, imine condensation, and imine reduction is described. This assisted tandem catalysis is catalyzed by B(C6F5)3 resulting in the first tandem Meinwald rearrangement-reductive amination protocol. The reaction proceeds in nondried solvents and yields β-functionalized amines. In particular, β-diarylamines are obtained in high yields.
Benzylic Ammonium Ylide Mediated Epoxidations
Roiser, Lukas,Robiette, Rapha?l,Waser, Mario
, p. 1963 - 1968 (2016/08/10)
A high yielding synthesis of stilbene oxides using ammonium ylides has been developed. It turned out that the amine leaving group plays a crucial role as trimethylamine gives higher yields than DABCO or quinuclidine. The amine group also influences the diastereoselectivity, and detailed DFT calculations to understand the key parameters of these reactions have been carried out.
A mild access to chiral syn 1,2-diaryl glycols by stereoselective ring opening of ortho substituted trans 2,3-diaryl-oxiranes using Amberlyst 15 in H2O/THF system
Lupattelli, Paolo,Chiummiento, Lucia,Funicello, Maria,Tramutola, Francesco,Marmo, Antonella,Gliubizzi, Natascia,Tofani, Daniela
supporting information, p. 5662 - 5668 (2015/08/03)
Amberlyst 15 was an efficient and green catalyst for the reaction of 2,3-diaryloxiranes with H2O in organic co-solvent to prepare glycols in high yield. Ortho substituted trans 2,3-diaryloxiranes afforded the corresponding syn glycols stereo- and enantiospecifically. Stereoselectivity appeared related to the coordination ability of the substituents, irrespective of their electronic properties. Indeed o-OCH3 and o-OBn substituted syn glycols were obtained in high stereochemical ratios (6/1 and 10/1, respectively), and o-OTIPS and o-NO2 substituted ones were obtained as exclusive products, with the same ee of the parent epoxides.
