38488-14-1Relevant academic research and scientific papers
Synthesis and x-ray structure of (1 Z,2 Z)-1,2-Bis(2-(phenylsulfonyl)-1-(4-tolyl)ethylidene)hydrazine
Abdel-Aziz, Hatem A.,Ghabbour, Hazem A.,Al-Rashood, Khalid A.,Fun, Hoong-Kun
, (2014)
The title compound (1Z,2Z)-1,2-bis(2-(phenylsulfonyl)-1-(4-tolyl)ethylidene)hydrazine (5) was prepared, in 78% yield, by the reaction of 2-(phenylsulfonyl)-1-(4-tolyl)ethan-1-one (3) with hydrazine hydrate in acetic acid at 90°C under microwave irradiatio
A glucose oxidase-hemoglobin system for efficient oxysulfonylation of alkenes/alkynes in water
Li, Chen,Li, Fengxi,Li, Zhengqiang,Liu, Jiaxu,Su, Jiali,Wang, Chunyu,Wang, Lei,Xu, Yaning,Yu, Yue
, (2020/12/29)
Background: β-ketosulfones are important bioactive compounds that have been extensively studied in organic chemistry. In this work, a green and efficient process for the synthesis of β-ketosulfones from alkenes (1) or alkynes (3) with sodium benzenesulfinate (2) was developed. Results: Under optimal conditions (alkenes (0.5 mmol) or alkynes (0.5 mmol), sodium benzenesulfinate (0.5 mmol), water (2 mL), hemoproteins (heme concentration: 0.06 mol%), GOX (42 U/ml), room temperature, 2 h), high yields of β-ketosulfones could be obtained when HgbRb (hemoglobin from rabbit blood) and GOX (glucose oxidase from Aspergillus niger) was used as the catalyst. Conclusion: This enzymatic method demonstrates the great potential for the synthesis of β-ketosulfones and extends the application of dual protein systems in organic synthesis.
Chemoenzymatic Oxosulfonylation-Bioreduction Sequence for the Stereoselective Synthesis of β-Hydroxy Sulfones
González-Sabín, Javier,Gotor-Fernández, Vicente,López-Agudo, Marina,Lavandera, Iván,Ríos-Lombardía, Nicolás
, (2021/08/23)
A series of optically active β-hydroxy sulfones has been obtained through an oxosulfonylation-stereoselective reduction sequence in aqueous medium. Firstly, β-keto sulfones were synthesized from arylacetylenes and sodium sulfinates to subsequently develop the carbonyl reduction in a highly selective fashion using alcohol dehydrogenases as biocatalysts. Optimization of the chemical oxosulfonylation reaction was investigated, finding inexpensive iron(III) chloride hexahydrate (FeCl3 ? 6H2O) as the catalyst of choice. The selection of isopropanol in the alcohol-water media resulted in high compatibility with the enzymatic process for enzyme cofactor recycling purposes, providing a straightforward access to both (R)- and (S)-β-hydroxy sulfones. The practical usefulness of this transformation was illustrated by describing the synthesis of a chiral intermediate of Apremilast. Interestingly, the development of a chemoenzymatic cascade approach avoided the isolation of β-keto sulfone intermediates, which allowed the preparation of chiral β-hydroxy sulfones in high conversion values (83–94 %) and excellent optical purities (94 to >99 % ee).
A Compartmentalized-type Bifunctional Magnetic Catalyst for One-pot Aerobic Oxysulfonylation and Asymmetric Transfer Hydrogenation
Wang, Shitong,Wang, Chengyi,Lv, Ning,Tan, Chunxia,Cheng, Tanyu,Liu, Guohua
, p. 909 - 915 (2020/11/30)
Utilization of the confined cavity of the mesoporous silica, the exploration of the synergetic catalysis process for sequential organic transformations has great significance in asymmetric catalysis. In this study, the yolk-shell-structured magnetic nanoparticles with the chiral Ru/diamine species within the nanochannels of the outer mesoporous silica shell and the FeCl3 species on the inner magnet core are fabricated. The electron microscopy images and the structural characterizations disclose the uniformly distributed magnetic nanoparticles with the well-defined single-site ruthenium/diamine active centers onto the outer silica shell. As a yolk-shell-structured bifunctional magnet catalyst, the FeCl3 species enables an efficient aerobic oxysulfonylation between aryl-substituted terminal alkynes and sodium sulfinates to the β-keto sulfones intermediates, and the ruthenium/diamine species sequentially reduces the in-situ generated intermediate to the chiral β-hydroxysulfones products. As we envision, this one-pot aerobic oxysulfonylation/asymmetric transfer hydrogenation process affords various chiral β-hydroxysulfones in high yields with excellent enantioselectivities. Furthermore, this magnetic catalyst can also be conveniently recovered via an additional outer magnet and repeatedly recycled, showing a potential application in industrial interest.
Oxidative Sulfonylation of Hydrazones Enabled by Synergistic Copper/Silver Catalysis
Xu, Jun,Shen, Chao,Qin, Xian,Wu, Jie,Zhang, Pengfei,Liu, Xiaogang
, p. 3706 - 3720 (2021/02/05)
A copper/silver-cocatalyzed protocol for oxidative sulfonylation of hydrazones is demonstrated. A wide range of β-ketosulfones and N-acylsulfonamides are directly synthesized in moderate to good yields. Our work provides a viable method for scalable preparation of β-ketosulfone derivatives that have found wide applications in the pharmaceutical industry.
Copper-catalyzed aerobic oxidative cross-coupling reactions of vinylarenes with sulfinate salts: A direct approach to β-ketosulfones
Chen, Yu,Xu, Lei,Wang, Biyu,Jiang, Jingjing,Sun, Yixiang,Li, Longchun
, (2021/01/25)
A copper-catalyzed aerobic oxidative cross-coupling reactions for the synthesis of β-ketosulfones via formation of a C[sbnd]S bond has been demonstrated. Promoted by the crucial copper catalyst, perfect selectivity and good to excellent yields could be achieved. This method, including inexpensive copper catalyst, wide functional group tolerance, and open air conditions, make it very attractive and practical. More importantly, it also provides a versatile tool for the construction of β-ketosulfones from basic starting materials under mild conditions.
Electrochemical Synthesis of β-Ketosulfones from Switchable Starting Materials
Yavari, Issa,Shaabanzadeh, Sina
supporting information, p. 464 - 467 (2020/01/31)
A synthesis of β-ketosulfones via sulfination of aryl methyl ketones and aryl acetylenes with sodium sulfinates under mild electrochemical conditions, in moderate to good chemical yields, is described. In particular, an electrochemical sulfination reaction of alkynes with sulfinate salts has never been explored. An environmentally friendly characteristic of this reaction is that it uses electricity as a valuable energy source for electrochemical synthesis of β-ketosulfones. This strategy is more convenient and practical compared to previous approaches.
One-pot synthesis of β-ketosulfones from sulfonyl chloride, hydrazine hydrate and vinyl azide in water
Zhang, Yaohong,Luo, Mengqiang,Li, Yan,Shen, Runfu,Qi, Chenze,Wang, Hai,Cheng, Kai
supporting information, (2020/10/26)
A novel, facile and efficient strategy for the one-pot synthesis of β-ketosulfones from readily available sulfonyl chloride, hydrazine hydrate and vinyl azides is described. The reaction proceeded very smoothly affording diverse β-ketosulfones in moderate to good yields. This new procedure has the advantages of environmental benign, easy and simple operation, low cost and wide tolerance of functional groups, which provides a highly fascinating protocol to access β-ketosulfones.
Photo-Mediated Decarboxylative Ketonization of Atropic Acids with Sulfonyl Hydrazides: Direct Access to β-Ketosulfones
Chen, Jie,Allyson, Zoe G.,Xin, Jing-Rui,Guan, Zhi,He, Yan-Hong
supporting information, p. 2045 - 2051 (2020/02/11)
An efficient formation of synthetically and biologically relevant β-ketosulfones via a photo-mediated decarboxylative ketonization of atropic acids was disclosed. The approach features metal-free conditions, good functional group compatibility, readily available starting materials and the use of ubiquitous dioxygen as both oxygen source and oxidant. Furthermore, mechanistic studies reveal that the decarboxylative ketonization reaction proceeds via a radical mechanism and may involve a radical chain reaction. (Figure presented.).
Method for preparing β-ketone sulfone compound through visible light-mediated atorvastatin decarboxylation reaction (by machine translation)
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Paragraph 0152-0157, (2020/04/29)
The preparation method of the invention has the characteristics β - that raw materials are simple and easy to obtain, the operation is simple . the reaction conditions are mild, and the reaction system is not sensitive to water . is a method for preparing,ketone sulfone compounds, by using environment-friendly (-source extensive atorvastatin as reactants), and then fully dissolving β -communicating oxygen balloon, in a mixed solvent of acetonitrile and water to obtain, ketal sulphone compounds by reacting, with a stable odorless sulfonyl hydrazide in a mixed solvent of acetonitrile and water under the irradiation of visible light. (by machine translation)
