405-18-5

Usage

Uses

Used in Pharmaceutical Synthesis:
(E)-2-phenylethenesulfonyl fluoride is used as a sulfonating agent for the synthesis of pharmaceuticals. Its reactivity allows for the creation of a wide range of drug molecules, making it a valuable tool in the development of new medications.
Used in Agrochemical Production:
In the agrochemical industry, (E)-2-phenylethenesulfonyl fluoride is utilized as a sulfonating agent in the production of various compounds. Its ability to react with different substrates contributes to the development of effective agrochemicals for agricultural applications.
Used in Organic Synthesis:
(E)-2-phenylethenesulfonyl fluoride is employed as a precursor for the production of other organosulfur compounds. Its unique reactivity enables the synthesis of a variety of organosulfur molecules, which are important in various chemical and industrial processes.
Used in Fluorination Reactions:
(E)-2-phenylethenesulfonyl fluoride has been studied for its potential use as a fluorinating agent in organic reactions. Its ability to introduce fluorine atoms into organic molecules can lead to the development of new compounds with unique properties and applications.

Upstream product

• 591-50-4 iodobenzene 
• 677-25-8 ethylenesulfonyl fluoride 
• 4091-26-3 β-styrenesulfonyl chloride 
• 100-42-5 styrene 
• 52147-97-4 trans 2-phenylethenesulfonyl chloride 
• 98-80-6 phenylboronic acid 
• 71-43-2 benzene 
• 5535-48-8 PVS 
• 2680-03-7 N,N-Dimethylacrylamide 
• 1629-58-9 4-penten-3-one 
• 107-13-1 acrylonitrile 
• 292638-85-8 acrylic acid methyl ester 

Relevant academic research and scientific papers

N-Heterocyclic Carbene Catalyzed Synthesis of δ-Sultones via α,β-Unsaturated Sulfonyl Azolium Intermediates

A limited array of reactive intermediates have enabled a wealth of discoveries in N-heterocyclic carbene organocatalysis. In this study, the viability of α,β-unsaturated sulfonyl azoliums as double electrophiles in new reactions is examined. Specifically,

Radical Fluorosulfonylation: Accessing Alkenyl Sulfonyl Fluorides from Alkenes

Sulfonyl fluorides have widespread applications in many fields. In particular, their unique biological activity has drawn considerable research interest in the context of chemical biology and drug discovery in the past years. Therefore, new and efficient methods for the synthesis of sulfonyl fluorides are highly in demand. In contrast to extensive studies on FSO2+-type reagents, a radical fluorosulfonylation reaction with a fluorosulfonyl radical (FSO2.) remains elusive so far, probably owing to its instability and difficulty in generation. Herein, the development of the first radical fluorosulfonylation of alkenes based on FSO2 radicals generated under photoredox conditions is reported. This radical approach provides a new and general access to alkenyl sulfonyl fluorides, including structures that would otherwise be challenging to synthesize with previously established cross-coupling methods. Moreover, extension to the late-stage fluorosulfonylation of natural products is also demonstrated.

Fluorosulfonyl free radical reagent, and preparation method and application thereof

The invention provides a fluorosulfonyl free radical reagent, and a preparation method and application thereof, and belongs to the technical field of organic synthesis. The fluorosulfonyl free radical reagent provided by the invention can efficiently generate fluorosulfonyl free radicals and carry out corresponding free radical reaction, and the product yield is high; the substrate adaptability of the fluorosulfonyl free radical reagent provided by the invention is extremely wide, and the fluorosulfonyl free radical reagent can react with various types of olefin substrates and alkyne substrates to efficiently synthesize sulfonyl fluoride products; meanwhile, the fluorosulfonyl free radical reagent provided by the invention is in a stable solid state at room temperature, is non-volatile, low in toxicity, easy to store and convenient to use, and has important academic and application values. In addition, the invention provides the preparation method of the fluorosulfonyl free radical reagent. The preparation method is simple to operate and suitable for large-scale production.

Preparation method of sulfuryl fluoride product

At present, reported reagents which can be used as compounds for direct sulfonylfluorination are mostly sulfonyl fluoride cation (FSO) reagents, but fluorosulfonyl free radical (FSO2) fluorosulfonylation reagents are not reported yet. The invention discloses application of sulfonyl fluoride chloride (SO2FCl) as a fluorosulfonyl free radical source for the first time, and fluorosulfonyl free radicals (FSO2) can be stably generated under various conditions, so a series of carbon-carbon double bonds or carbon-carbon triple bonds can be subjected to addition to prepare polysubstituted vinylsulfonyl fluoride compounds. The free radical fluorosulfonylation method is expected to be widely applied to the fields of organic synthesis, drug development, high polymer materials and the like.

Synthesis of β-Arylethenesulfonyl Fluoride via Pd-Catalyzed Nondirected C-H Alkenylation

A rapid synthesis of β-arylethenesulfonyl fluorides is realized using ligand-accelerated Pd(II)-catalyzed nondirected C-H alkenylation of simple arenes. The newly developed electron-deficient 2-pyridone ligand is crucial for this transformation with arenes as limiting reagent. This protocol features a broad substrate scope and good functional group tolerance. Late-stage functionalization of various pharmaceuticals and their further click manipulations demonstrate this procedure to be highly valuable.

Directed ortho-Metalation of Arenesulfonyl Fluorides and Aryl Fluorosulfates

Studies on directed ortho -metalation (DoM) of arenesulfonyl fluorides (ArSO 2 F) with in situ electrophile trapping are presented. Under optimized conditions (LDA, THF, -78 °C), a series of model substrates was mono- and difunctionalized with trimethylsilyl chloride in good yields. The synthetic results reveal powerful directing character of the SO 2 F group, being ahead of bromine and methoxy substituents. Under the same metalation conditions, aryl fluorosulfates (ArOSO 2 F) display fragmentation to arynes and migration of the SO 2 F group to the ortho position (anionic thia-Fries rearrangement).

Converting (E)-(Hetero)arylethanesulfonyl Fluorides to (Z)-(Hetero)arylethanesulfonyl Fluorides Under Light Irradiation

The construction of (Z)-(hetero)arylethenesulfonyl fluorides was achieved utilizing Iridium photoredox catalysis under UV-light irradiation. This protocol provided a diverse range of (Z)-(hetero)arylethenesulfonyl fluorides in moderate to good yields under mild conditions without external additives. The late-stage transformation of the (Z)-(hetero)arylethenesulfonyl fluorides comparing with their E-configuration counterparts was also studied.

[3+2] Cycloaddition of an Azomethyne Ylide and Vinyl Sulfonyl Fluorides ― an Approach to Pyrrolidine-3-sulfonyl Fluorides

[3+2] Cycloaddition reactions of vinyl sulfonyl fluorides with an in-situ generated nonstabilized azomethine ylide is described for the first time. The resulting pyrrolidine-3-sulfonyl fluorides were obtained in 50–83 % yield on a scale of up to 25 g. Their utility as reagents for sulfur(VI)–fluoride exchange (SuFEx) and some other transformations was also demonstrated.

Preparation method of 2-aryl-ethenylsulfonyl chloride compound

The invention discloses a preparation method of 2-aryl-ethenylsulfonyl chloride compound, comprising the steps of using arylboronic acid, arylboronic acid ester or arylboronic acid salt as a raw material, mixing with ESF (ethenylsulfonyl chloride), palladium catalyst, an oxidant and a solvent, allowing reacting at 20-120 DEG C for 2 h and longer, separating and purifying to obtain an ethenylsulfonyl chloride product. A molar ratio of arylboronic acid (ester) and its salt, ethenylsulfonyl chloride, the palladium catalyst and the oxidant is 1:(1-10):(0.000001-0.2):(0.5-5). The preparation method has the advantages that raw materials are simple and easy to obtain, large-scale commercial supply is available for both arylboronic acid (ester) and its salt, the arylboronic acid (ester) and its salt are tolerant to most functional groups and good in reaction selectivity (both bromine and chlorine substituent on aryl are not involved in the reaction under same reaction conditions), and the preparation method has good technical potential in large-scale preparation in labs and industrial amplified production.

Gram-Scale Synthesis of β-(Hetero)arylethenesulfonyl Fluorides via a Pd(OAc)2 Catalyzed Oxidative Heck Process with DDQ or AgNO3 as an Oxidant

A practical oxidative Heck reaction between organoboronic acids and ethenesulfonyl fluoride (ESF) is developed. Aryl- and heteroaryl-boronic acids react efficiently and stereoselectively with ESF in the presence of a catalytic amount of Pd(OAc)2 and 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ) or AgNO3 in AcOH to afford the corresponding E-isomer of β-arylethenesulfonyl fluoride products. The utility of this reaction is exemplified by an expanded scope of 47 examples including N-, O-, and S-containing heteroaromatics, demonstrating chemoselectivity over aryliodides, and gram-scale operation without the requirement for strict anhydrous or oxygen-free conditions. Furthermore, this procedure discriminates against the formation of arylboronic acids homo-coupling byproducts. In addition, the preparation of the first aryl vinylsulfonate polymer, a material with functionalizable Michael acceptor sites, from a starting arylboronic acid is described. (Figure presented.).