30158-44-2

Usage

Chemical structure

1-[(2-chloro-2-phenylethyl)sulfonyl]-4-fluorobenzene is a sulfonyl fluoride consisting of a benzene ring with a fluorine atom at the para position and a sulfonyl chloride with a 2-chloro-2-phenylethyl substituent at the para position.

Functional groups

The compound contains a sulfonyl fluoride group, a benzene ring, a fluorine atom, a sulfonyl chloride group, and a 2-chloro-2-phenylethyl substituent.

Reactivity

It is a reactive compound, which makes it a versatile building block in organic synthesis.

Applications

The compound is used in the synthesis of various pharmaceuticals and agrochemicals.

Unique structure

Its unique structure allows for the introduction of diverse functional groups and the modification of biological activities.

Synthetic intermediate

Due to its reactivity and ability to serve as a synthetic intermediate, it is a valuable tool for creating complex organic molecules.

Field of use

It is particularly used in the field of medicinal chemistry and drug development.

Upstream product

• 100-42-5 styrene 
• 349-88-2 4-Fluorobenzenesulfonyl chloride 
• 459-45-0 4-fluorobenzenediazonium tetrafluoroborate 

Relevant academic research and scientific papers

Copper-Catalyzed Chloro-Arylsulfonylation of Styrene Derivatives via the Insertion of Sulfur Dioxide

A copper-catalyzed four-component chloro-arylsulfonylation of styrene derivatives with aryldiazonium tetrafluoroborates, lithium chloride, and ex-situ generated sulfur dioxide (from SOgen) is presented. This sulfonylation features good functional group compatibility, mild reaction conditions, excellent regioselectivity, and good yields. The robustness and potential of this method have also been successfully demonstrated by a gram-scale reaction. Based on experimental study, a radical-involved mechanism is proposed for the transformation.

Visible-Light-Mediated Regioselective Chlorosulfonylation of Alkenes and Alkynes: Introducing the Cu(II) Complex [Cu(dap)Cl2] to Photochemical ATRA Reactions

A visible-light-mediated photocatalyzed protocol utilizing copper-phenanthroline-based catalysts has been developed that can convert a large number of olefins into their chlorosulfonylated products. Besides the Cu(I) complex [Cu(dap)2]Cl, now well-established in photo-ATRA processes, the corresponding Cu(II) complex [Cu(dap)Cl2] proved to be often even more efficient in the title reaction, being advantageous from an economic point of view but also opening up new avenues for photoredox catalysis. Moreover, the copper complexes outperformed commonly used ruthenium, iridium, or organic dye based photocatalysts, owing to their ability to stabilize or interact with transient radicals by inner sphere mechanisms. The use of stoichiometric Na2CO3 in combination with the copper photocatalysts was found to be essential to convert unactivated olefins to the desired products, in contrast to activated olefins for which no additive was required. As suggested by appropriate control experiments, the role of Na2CO3 is attributed to prevention of poisoning of the catalyst.

Cu-Catalyzed photoredox chlorosulfonation of alkenes and alkynes

Visible-light photoredox chlorosulfonation of alkenes and alkynes is achieved using a Cu photocatalyst. The reactions occur under mild conditions, have broad scope, and have high functional group tolerance.

Arenesulfonyl halides: A universal class of functional initiators for metal-catalyzed 'living' radical polymerization of styrene(s), methacrylates, and acrylates

The complex Cu(I)Cl/4,4'-dinonyl-2,2'-bipyridine (bpy9) catalyzes via a redox process the homogeneous 'living' radical polymerization of styrene(s), methacrylates, and acrylates initiated with a variety of functional phenylsulfonyl chlorides. Polymers with narrow molecular weight distribution and molecular weights close to the theoretical ones are obtained from these three classes of monomers. Kinetics of propagation and initiation were performed with selected substituted phenylsulfonyl chlorides and with their monoadducts to monomer. Polymerizations follow first-order kinetics internally in monomer and externally in Cu(I)Cl while initiation is first order internally in initiator and in Cu(I)Cl concentrations. A catalyst concentration dependence of the optimum bpy9/Cu(I)Cl ratio which yields the largest rate constant of polymerization was observed. The apparent rate constants of propagation corrected for catalyst concentration are in the order: methacrylates > styrene > acrylates. This inversion from the classic dependence of the corresponding absolute rate constants (acrylates > methacrylates > styrene) was shown to be determined by a different steady-state concentration of propagating radicals which is in dynamic equilibrium with an extremely large excess of the corresponding dormant C-Cl species. The formation and the concentration of the radical species is determined by the C-Cl bond strength of the dormant species. Apparent rate constants of initiation corrected for catalyst concentration are in the order: styrene > methacrylates > acrylates. Within experimental error, initiation efficiency is 100% and the apparent rate constants of initiation are 4 (for styrene and methacrylates) and 3 or 2 (for acrylates) orders of magnitude higher than those of propagation. The absence of conjugation between the sulfonyl radical and its phenyl group generates a small effect of the phenyl group substituent on the rate constant of initiation. These results demonstrate that arenesulfonyl chlorides are the first class of universal functional initiators for the metal-catalyzed 'living' radical polymerization of styrene(s), methacrylates, and acrylates. This discovery provides numerous fundamental and technological opportunities in the field of controlled radical polymerization and copolymerization, of well-defined functional polymers and copolymers with complex architecture, and of self-organized supramolecular systems based on them. The experimental results demonstrate that arenesulfonyl halides, are the first class of universal functional initiators for the metal-catalyzed living radical polymerization of styrene(s), methacrylates and acrylates. This discovery provides numerous fundamental and technological opportunities in the field of controlled radical polymerization and copolymerization, of well-defined functional polymers and copolymers with complex architecture, and of self-organized supramolecular systems based on them.