1260149-74-3

Upstream product

• 186405-37-8 2-((4-(trifluoromethyl)phenyl)sulfonyl)acetonitrile 
• 98-80-6 phenylboronic acid 
• 1230154-76-3 C₉H₆F₃NS 
• 825-83-2 4-trifluoromethylbenzenethiol 
• 19433-17-1 acetophenone O-acetyloxime 
• 57957-24-1 N-(1-phenylvinyl)acetamide 
• 637-44-5 phenylpropyolic acid 
• 70-11-1 α-bromoacetophenone 
• 100-42-5 styrene 
• 829-70-9 4-(trifluoromethyl)benzenesulfinic acid 
• 492-38-6 2-phenylacrylic acid 
• 536-74-3 phenylacetylene 
• 16717-64-9 1-azidostyrene 
• 948-97-0 2,3-diphenyl-1-propene 

Relevant academic research and scientific papers

Oxy-sulfonylation of terminal alkynesviaC-S coupling enabled by copper photoredox catalysis

We report the first literature example using visible light-induced trimethylsilyl azide (TMS-N3)-assisted copper-catalyzed oxy-sulfonylation of terminal C-C bonds to form β-keto sulfones (C-S bond formation). TMS-N3promotes the reaction by facilitating the formation of sulfonyl radicals, which later decompose into N2gas upon light irradiation. This method involves the use of commercially available and stable starting materials. Also, a wide range of functional groups have been well-tolerated under the current photoredox process, evading the side product formation. Potent biologically active compounds, such as CES1, 11β-HSD1 inhibitors, anti-analgesic agents, and reactive synthesis intermediates were synthesized to demonstrate the synthetic utility of the current methodology. Moreover, green chemistry metrics and Eco-scale evaluation for the current photochemical method show that the protocol is eco-friendly and highly efficient.

Cu(OTf)2-Catalyzed efficient sulfonylation of vinyl azides with sodium sulfinates

A simple oxidative cross-coupling reaction between vinyl azides and sodium sulfinates was developed. This reaction uses commercial arylsulfinates that are more efficient, cheaper, and more stable as sulfonylation reagents, for efficiently, cheaply, and environmentally friendly synthesis of β-keto sulfones. And the reaction has the advantages of simple operation, high efficiency, good yield, and also has a wide range of functional group tolerance.

Copper-Catalyzed Aerobic Oxidative Cleavage of Unstrained Carbon-Carbon Bonds of 1,1-Disubstituted Alkenes with Sulfonyl Hydrazides

Alkoxy radical-mediated carbon-carbon bond cleavages have emerged as a powerful strategy to complement traditional ionic-type transformations. However, carbon-carbon cleavage reaction triggered by alkoxy radical intermediate derived from the combination of alkyl radical and dioxygen, is scarce and underdeveloped. Herein, we report alkoxy radical, which was generated from alkyl radical and dioxygen, mediated selective cleavage of unstrained carbon-carbon bond for the oxysulfonylation of 1,1-disubstituted alkenes, providing facile access to a variety of valuable β-keto sulfones. Mechanistic experiments indicated alkoxy radical intermediate that underwent subsequent regioselective β-scission might be involved in the reaction and preliminary computational studies were conducted to provide a detailed explanation on the regioselectivity of the C—C bond cleavage. Notably, the strategy was successfully applied for constructing uneasily obtained architecturally intriguing molecules.

Photosensitizer-free synthesis of β-keto sulfones: Via visible-light-induced oxysulfonylation of alkenes with sulfonic acids

A practical and environment-friendly methodology for the construction of β-keto sulfones through visible-light induced direct oxysulfonylation of alkenes with sulfonic acids at ambient temperature under open-air conditions was developed. Most importantly, the reaction proceeded smoothly without the addition of any photocatalyst or strong oxidant, ultimately minimizing the production of chemical waste.

Preparation method of beta-carbonyl sulfone compound

The invention discloses a preparation method of a beta-carbonyl sulfone compound, and belongs to the technical field of organic synthesis. The preparation method of the beta-carbonyl sulfone compoundis provided for solving the problems that in the prior art, operation is complex, the substrate range is narrow, and the functional group tolerance is poor. The preparation method comprises the stepsof taking a compound shown in formula I and a compound shown in formula II as raw materials, taking copper salt as a catalyst, carrying out reaction in an organic solvent, and after the reaction is completed, carrying out aftertreatment to obtain the beta-carbonyl sulfone compound. The preparation method is simple and convenient to operate, mild in reaction condition, wide in substrate range and good in functional group tolerance, the yield reaches up to 93%, and the synthesis cost is remarkably reduced.

Photo-Mediated Decarboxylative Ketonization of Atropic Acids with Sulfonyl Hydrazides: Direct Access to β-Ketosulfones

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)

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)

Biomimetic photocatalytic sulfonation of alkenes to access β-ketosulfones with single-atom iron site

Biomimetic photocatalysis as an important organic transformation strategy has received increasing attention, with the performances of biomimetic catalysts largely depending on their design. This protocol has been initially used to fabricate a biomimetic photocatalyst of single-atom iron site through coupling carbon nitride with hemin (CNH) for the visible light-promoted sulfonation of alkenes to produce β-ketosulfones with up to 94% yield. The experimental results show that the role of CN in CNH is concentrated on enhancing the separation ability of photogenerated electron pairs and holes to improve the photocatalytic activity and stability. Moreover, the as-prepared photocatalyst of single atom iron can be irradiated under near-infrared light with a satisfactory yield, and is also feasible for the sulfonation reactions of androstenones. Importantly, this biomimetic catalysis-based synthesis system has some merits, namely high catalysis efficiency, favorable recyclability, high turnover number, and excellent functional group tolerance, making it promising for extensive applications in organic transformations for the synthesis of β-ketosulfones to access various bioactive drugs.

A Naphthalimide-Based ND-O-EAc Photocatalyst for Sulfonation of Alkenes to Access β-Ketosulfones Under Visible Light

The development of facile, efficient, cost-effective, and visible light-driven photocatalysts for organic synthetic chemistry has received increasing attention. This protocol has initially synthesized a naphthalimide-based ND-O-EAc visible light photocatalyst for the sulfonation of alkenes to produce β-ketosulfones. Compared with the current photosynthetic strategies, the newly developed catalytic system has some merits, namely high efficiency, gram-scale preparation of low-cost photocatalyst, no metal contamination, wide substrate scope, and green terminal oxidant of air. Moreover, the prepared photocatalyst of ND-O-EAc is feasible for the sulfonation reactions of androstenones. Importantly, such a photocatalysis strategy can easily realize the scale-up synthesis for β-ketosulfone drugs under the mild conditions up to 90 % yield.

Heterogeneous copper-catalyzed oxidative coupling of oxime acetates with sodium sulfinates: An efficient and practical synthesis of β-keto sulfones

An efficient and practical route to β-keto sulfones has been developed through heterogeneous oxidative coupling of oxime acetates with sodium sulfinates by using an MCM-41-supported Schiff base-pyridine bidentate copper (II) complex [MCM-41-Sb,Py-Cu (OAc)2] as the catalyst and oxime acetates as an internal oxidant, followed by hydrolysis. The reaction generates a variety of β-keto sulfones in good to excellent yields. This new heterogeneous copper (II) catalyst can be easily prepared via a simple procedure from readily available and inexpensive reagents and exhibits the same catalytic activity as Cu (OAc)2. MCM-41-Sb,Py-Cu (OAc)2 is also easy to recover and is recyclable up to eight times with almost consistent activity.