16212-06-9

Usage

Uses

Phenyl trans-beta-styryl sulfone is used as a building block for proteomics research.

Synthesis Reference(s)

Synthetic Communications, 19, p. 2209, 1989 DOI: 10.1080/00397918908052616Tetrahedron Letters, 25, p. 3203, 1984 DOI: 10.1016/S0040-4039(01)91008-1

InChI:InChI=1/C14H12O2S/c15-17(16,14-9-5-2-6-10-14)12-11-13-7-3-1-4-8-13/h1-12H/b12-11-

Upstream product

• 108-98-5 thiophenol 
• 536-74-3 phenylacetylene 
• 67-56-1 methanol 
• 32291-77-3 phenyl (Z)-β-styryl sulphone 
• 591-50-4 iodobenzene 
• 88486-41-3 1-(tri-n-butylstannyl)-2-(phenylsulfonyl)ethene 
• 64-17-5 ethanol 
• 4110-77-4 (E)-β-chlorostyrene 
• 100-34-5 benzene diazonium chloride 
• 124-41-4 sodium methylate 
• 141-52-6 sodium ethanolate 
• 17872-92-3 (phenylsulfonylmethyl)trimethylsilane 
• 108-24-7 acetic anhydride 
• 100-52-7 benzaldehyde 

Downstream Products

• 65885-20-3 (2-benzenesulfonyl-1-phenyl-ethyl)-dimethyl-amine 
• 128593-04-4 1-phenyl-2-(benzenesulphonyl)-1-(1-pyrrolidyl)ethane 
• 87289-94-9 (3R,4R,5S)-4-Benzenesulfonyl-2,3,5-triphenyl-isoxazolidine 
• 69333-48-8 1-phenyl sulphonyl-2-methoxy-2-phenyl ethane 
• 82884-24-0 3-Benzenesulfonyl-2,6-diphenyl-2,3,4,7-tetrahydro-1H-azepine 
• 65885-18-9 phenyl (2-phenyl-2-ethoxy ethyl)sulphone 
• 16037-44-8 4-phenyl-3-trimethylsilylpyrazole 
• 3846-66-0 (E)-1-tert-butyl-2-phenylethene 
• 3846-66-0 β-tert-butylstyrene 
• 113303-16-5 3,3-dimethyl-2-phenylbutyl phenyl sulfone 
• 3740-05-4 (Z)-1-(3,3-dimethylbut-1-enyl)benzene 
• 117917-66-5 C₂₂H₂₃⁽²⁾HO₂SSi 
• 117917-66-5 C₂₂H₂₃⁽²⁾HO₂SSi 
• 15325-61-8 3-methyl-1-phenyl-1-butene 

Relevant academic research and scientific papers

ORGANIC SYNTHESIS WITH SULFONES XXXII. A CONVENIENT ROUTE TO α,β-UNSATURATED SULFONES FROM SATURATED SULFONE

α-sulfonyl lithiated anions are oxidized by cupric carboxylates into α,β-unsaturated sulfones.Primary sulfones lead to pure trans-vinylic sulfones.

Facile method for solid-phase synthesis of vinyl sulfones using polystyrene-supported selenomethyl aryl sulfone

Treatment of novel polystyrene-supported selenomethyl aryl sulfone with LDA followed by alkylation and oxidation elimination efficiently afforded vinyl sulfones in good yields and purities.

Controlled Synthesis of β-Keto Sulfones and Vinyl Sulfones under Electrochemical Oxidation

Selective sulfonylation and oxosulfonylation of alkenes with sulfinates have been developed via anodic oxidation in an undivided cell. The novel electrosynthetic method provided β-keto sulfones and vinyl sulfones with good to excellent yields in the absence of any transition metal catalyst and oxidants. Mechanism studies show that two different pathways involved in these two transformations.

Visible-Light-Induced Three-Component Intermolecular Trifluoromethyl-Alkenylation Reactions of Unactivated Alkenes

Herein, we describe a practical protocol for efficient, mild, visible-light-induced three-component intermolecular trifluoromethyl-alkenylation reactions of unactivated alkenes. The protocol has good functional group tolerance and a broad substrate scope. Using this protocol, we not only introduced a trifluoromethyl group into alkenes but also converted unactivated alkenes to styrene-based activated alkenes, in addition to accomplishing late-stage functionalization of pharmaceutical intermediates. (Figure presented.).

Visible-Light-Mediated Alkenylation of Alkyl Boronic Acids without an External Lewis Base as an Activator

Herein we report a protocol for the direct visible-light-mediated alkenylation of alkyl boronic acids at room temperature without an external Lewis base as an activator, and we propose a mechanism involving benzenesulfinate activation of the alkyl boronic acids. The protocol permits the efficient functionalization of a broad range of cyclic and acyclic primary and secondary alkyl boronic acids with various alkenyl sulfones. We demonstrated its utility by preparing or functionalizing several pharmaceuticals and natural products.

Intermolecular [2 + 2] Photocycloaddition of α,β-Unsaturated Sulfones: Catalyst-Free Reaction and Catalytic Variants

2-Aryl-1-sulfonyl-substituted cyclobutanes were prepared in an intermolecular [2 + 2] photocycloaddition from various α,β-unsaturated sulfones and olefins upon irradiation at λ = 300 nm (26 examples, 60-99% yield). Lewis acids catalyzed the [2 + 2] photocycloaddition of 2-benzimidazolyl styryl sulfones. At short wavelengths, the latter substrates underwent C-S bond cleavage but AlBr3 (5 mol %) allowed for an intermolecular reaction with 2,3-dimethyl-2-butene at longer wavelengths. A chiral-at-metal Lewis acid (2 mol %) facilitated an enantioselective reaction (up to 77% ee).

Selective synthesis of sulfoxides and sulfonesviacontrollable oxidation of sulfides withN-fluorobenzenesulfonimide

A practical and mild method for the switchable synthesis of sulfoxides or sulfonesviaselective oxidation of sulfides using cheapN-fluorobenzenesulfonimide (NFSI) as the oxidant has been developed. These highly chemoselective transformations were simply achieved by varying the NFSI loading with H2O as the green solvent and oxygen source without any additives. The good functional group tolerance makes the strategy valuable.

PhB(OH)2-Promoted Electrochemical Sulfuration-Formyloxylation of Styrenes and Selectfluor-Mediated Oxidation-Olefination

We report a PhB(OH)2-promoted electrochemical sulfuration-formyloxylation reaction of styrenes employing commercially available thiophenols/thiols as thiolating agents. Specifically, metal catalysts and external chemical oxidants are not needed in the reaction for the formation of β-formyloxy sulfides, and these sulfides can be further converted to (E)-vinyl sulfones via the Selectfluor-mediated oxidation-olefination. Notably, on the basis of this electrochemical oxidation strategy, β-hydroxy sulfide, β-formyloxy sulfoxide, β-formyloxy sulfone, and (E)-vinyl sulfoxide can also be easily prepared.

Vinyl sulfone synthesisviacopper-catalyzed three-component decarboxylative addition

The synthesis of vinyl sulfone derivativesviathe reaction of arylpropiolic acids, K2S2O5, and aryl boronic acids is reported. The CuBr2/1,10-phenanthroline catalytic system in the presence of acetic acid provide

Synthesis of (E)-iodo vinylsulfones via oxidative addition of thiol into alkyne under metal free condition

An efficient, transition-metal free and molecular iodine promoted protocol for the construction of (E)-β-iodovinyl sulfone derivatives via oxidative C–S coupling of thiol and alkyne has been demonstrated. Both aryl and alkyl terminal acetylenes were found to be an excellent substrate for the present reaction which provides a wide range of β-iodovinyl sulfone derivatives with very good yield and excellent regio and stereo-selectivities. Diaryldisulfide is also found to be an equally efficient sulfonyl group surrogate under identical reaction conditions.