49833-39-8

Upstream product

• 40824-70-2 (2-Benzenesulfonyl-2-phenyl-ethyl)-trimethyl-ammonium 
• 100-42-5 styrene 
• 873-55-2 sodium benzenesulfonate 
• 7476-66-6 methyl 2-chloro-2-phenylethanoate 
• 536-74-3 phenylacetylene 
• 618-41-7 Benzenesulfinic acid 
• 17101-78-9 <(1-bromoethenyl)sulfonyl>benzene 
• 98-80-6 phenylboronic acid 
• 102921-26-6 (1,2-dibromoethyl)benzene 
• 100-39-0 benzyl bromide 
• 50-00-0 formaldehyd 
• 3112-88-7 Benzyl phenyl sulfone 
• 96-09-3 styrene oxide 
• 51256-38-3 methyl α-phenyl-α-(phenylthio)acetate 

Downstream Products

• 53876-79-2 1,2-bis-benzenesulfonyl-1-phenyl-ethane 
• 65885-17-8 C₁₆H₁₈O₃S 
• 24422-78-4 phenyl α-methylbenzyl sulfone 
• 34782-55-3 1-phenyl-1-(benzenesulphonyl)cyclopropane 
• 16212-06-9 phenyl styryl sulfone 
• 30166-85-9 1-fluoro-4-[(E)-2-phenylethenesulfonyl]benzene 
• 29290-75-3 C₂₀H₁₈O₂S₂ 

Relevant academic research and scientific papers

Base-controlled divergent synthesis of vinyl sulfones from (benzylsulfonyl)benzenes and paraformaldehyde

A tuneable metal-free protocol for the selective preparation of a-substituted vinyl sulfone and (E)-vinyl sulfone derivatives has been described. In this process, stable paraformaldehyde was used as the carbon source. The base played an important role in the selectivity control of transformations. More than 50 products were synthesized with excellent chemoselectivity and broad functional group tolerance.

Johnson-Corey-Chaykovsky fluorocyclopropanation of double activated alkenes: Scope and limitations

Johnson-Corey-Chaykovsky fluorocyclopropanation of double activated alkenes utilizing S-monofluoromethyl-S-phenyl-2,3,4,5-tetramethylphenylsulfonium tetrafluoroborate is an efficient approach to obtain a range of monofluorocyclopropane derivatives. So far, fluoromethylsulfonium salts have displayed the broadest scope for direct fluoromethylene transfer. In contrast to more commonly used fluorohalomethanes or freon derivatives, diarylfluoromethylsulfonium salts are bench stable, easy-to use reagents useful for the direct transfer of a fluoromethylene group to alkenes giving access to the challenging products-fluorocyclopropane derivatives. Interplay between the reactivity of the starting materials and stability of the fluorocyclopropanes formed determines the outcome of the process.

Markovnikov-Selective Radical Addition of S-Nucleophiles to Terminal Alkynes through a Photoredox Process

Direct radical additions to terminal alkynes have been widely employed in organic synthesis, providing credible access to the anti-Markovnikov products. Because of the Kharasch effect, regioselective control for the formation of Markovnikov products still remains a great challenge. Herein, we develop a transition-metal-free, visible light-mediated radical addition of S-nucleophiles to terminal alkynes, furnishing a wide array of α-substituted vinyl sulfones with exclusive Markovnikov regioselectivity. Mechanistic investigations demonstrated that radical/radical cross-coupling might be the key step in this transformation. This radical Markovnikov addition protocol also provides an opportunity to facilitate the synthesis of other valuable α-substituted vinyl compounds.

An efficient and straightforward route to terminal vinyl sulfones via palladium-catalyzed Suzuki reactions of α-bromo ethenylsulfones

A general and simple protocol for the synthesis of α-substituted alkenylsulfones has been developed firstly via palladium-catalyzed Suzuki reactions between α-bromo ethenylsulfones and organoborons. Using a catalyst composed of Pd(OAc)2 and SPhos, a variety of aryl, heteroaryl, and alkylboron reagents could efficiently couple with α-bromo ethenylsulfones under mild conditions. Moreover, it has been demonstrated for the first time that vinyl sulfones underwent smooth reduction by diimide generated from 2-nitrobenzenesulfonylhydrazide.

Method for catalytically synthesizing alpha-aryl vinyl sulphone by aid of Pd

The invention discloses a method for catalytically synthesizing alpha-aryl vinyl sulphone by the aid of Pd. The method includes particular steps of adding alpha-vinyl bromide sulphone, arylboronic acid, palladium acetate, cesium carbonate and Sphos into a reactor; vacuumizing the reactor and filling the reactor with nitrogen to remove oxygen; adding anhydrous toluene into the reactor in protection of the hydrogen and stirring the anhydrous toluene at the temperature of 50-80 DEG C for 10-20 h; carrying out reaction to obtain reaction mixtures, and then enabling the reaction mixtures to flow through silica gel columns to remove inorganic salt by the aid of ethyl acetate which is an eluting agent so as to obtain eluent; rotationally evaporating the eluent to remove the ethyl acetate and the toluene, then carrying out column chromatography separation on the eluent by the aid of petroleum ether and ethyl acetate mixed liquid which is used as an eluting agent and ultimately distilling the eluent to obtain the alpha-aryl vinyl sulphone. The method has the advantages of excellent universality of substrates, high compatibility of functional groups, mild reaction conditions and high reaction efficiency.

Gold-catalyzed intermolecular C-S bond formation: Efficient synthesis of α-substituted vinyl sulfones

A general method for the synthesis of α-substituted vinyl sulfones makes use of a combination of a triazole gold complex and gallium triflate. This efficient C-S bond formation between simple terminal alkynes and sulfinic acids provides access to various α-substituted vinyl sulfones. Less basic, less hindered: The gold-catalyzed intermolecular Markovnikov addition of sulfinic acids to terminal alkynes has been achieved through the use of a bimetallic gold/gallium catalyst system. Various α-substituted vinyl sulfones were efficiently synthesized. A one-pot synthesis that starts from the bench-stable sodium sulfinates was also developed (DCE=1,2-dichloroethane).

A one-pot regioselective synthetic route to vinyl sulfones from terminal epoxides in aqueous media

A highly efficient LiBr catalysed regioselective synthesis of vinyl sulfones from readily available terminal epoxides and sodium sulfinates in a one-pot procedure using water as a reaction medium is reported. The protocol is adorned with several attributes of green chemistry like recycling of the catalyst, atom-economy and an aqueous medium.

Polystyrene-supported selenosulfonates: Efficient reagents for regio- and stereocontrolled synthesis of vinyl sulfones

Two novel polystyrene-supported selenosulfonates reagents have been developed. As reagents for boron trifluoride catalyzed or AIBN catalyzed addition to olefins were successfully demonstrated and have been used for regioselective synthesis of vinyl sulfon

Solvolytic Generation of α-Sulfonyl and α-Sulfinyl Carbocations

A series of mesylates of general type ArC(CH3)(SO2Ph)OMs, 14, have been prepared and studied under solvolytic conditions.The Hammett p value in methanol is -7.98.A solvent effect study on 14b, where Ar=p-CH3C6H4, gave a good correlation with YOTs values and an m value of 0.85.These data were interpreted in terms of the involvement of α-sulfonyl-substituted carbocations, which have a large demand for aryl group stabilization.In solvolyses of 14b, capture of the α-sulfonyl carbocation by acetic or trifluoroacetic acid gave simple substitution products which could be isolated.In alcohol solvents subsequent unimolecular loss of benzenesulfinate ion from the initially formed α-alkoxy sulfone led ultimately to the formation of ketones or ketals.Analogous loss of benzenesulfinate from the primary product is also seen on prolonged reaction of 14b in carboxylic acid solvents.Solvolyses of a series of α-bromo sulfoxides of general structure ArC(CH3)(SOPh)Br, 35, also proceed via the intermediacy of carbocations.The demand for aryl stabilization in these α-sulfinyl cations is also quite large as evidenced by the p value of -7.18 in trifluoroethanol.The trifluoroethanolysis rate of 35b, where Ar=p-CH3C6H4, is 1.4x105 times slower at 25 deg C than that of the α-H analogue ArCH(CH3)Br, 29.This, along with the large negative p value, implies that the interaction of the sulfur nonbonding electrons with the adjacent cationic center is of minimal importance in the α-sulfinyl carbocation derived from 35b.These data conflict with previous suggestion that α-sulfinyl cations are greatly stabilized by the sulfur nonbonding electrons.Suggestions are offered to explain this apparent conflict.The relative reactivities of a series of bromides containing electron-withdrawing groups have been determined in the common solvent trifluoroethanol in order to evaluate the effect of these groups on the rate of carbocation generation.The relative reactivity order for sovolyses of substrates of general type p-CH3C6H4C(CH3)BrE, where E is an electronegative group, is COPh>PO(OEt)2>CN>SOPh>CF3>SO2Ph.

Synthesis of Alkenes via Peterson Reaction

The α-phenylthiosilanes (2) have been used to prepare the α-silyl anions (1) by reaction with lithium naphthalenide; subsequent condensation with a carbonyl compound gave the alkene (8) via the Peterson reaction.The α-phenylthiosilanes (2) were prepared from n,n-bis(phenylthio)acetals (4) by reaction with lithium naphthalenide and chlorotrimethylsilane.The n,n-bis(phenylthio)acetals (4) were obtained, in turn, from 1,1-bis(phenylthio)acetals (5) by anion formation with butyl-lithium-N,N,N',N'-tetramethylethylenediamine complex in hexane followed by reaction with an alkyl halide.The Peterson reaction was also used to prepare vinyl sulphides (9) and vinyl sulphones (13).