16212-08-1

Usage

Synthesis Reference(s)

Chemistry Letters, 15, p. 289, 1986Journal of the American Chemical Society, 102, p. 7603, 1980 DOI: 10.1021/ja00545a054The Journal of Organic Chemistry, 45, p. 406, 1980 DOI: 10.1021/jo01291a006

InChI:InChI=1/C15H14O2S/c1-13-7-9-15(10-8-13)18(16,17)12-11-14-5-3-2-4-6-14/h2-12H,1H3/b12-11+

Upstream product

• 3937-96-0 tosylacetic acid 
• 100-52-7 benzaldehyde 
• 100-42-5 styrene 
• 459-44-9 4-methylbenzenediazonium tetrafluoroborate 
• 98-59-9 p-toluenesulfonyl chloride 
• 24182-83-0 (E)-styryl(p-tolyl)sulfane 
• 3185-99-7 Methyl p-tolyl sulfone 
• 76649-85-9 1-Phenyl-1-(phenylseleno)-2-(p-toluenesulfonyl)ethane 
• 66680-87-3 (E)-1-phenyl-(2-tributylstannyl)ethene 
• 19372-00-0 1-(trimethylsilyl)-2-phenylethene 
• 824-79-3 sodium 4-methylbenzenesulfinate 
• 28995-88-2 1-methyl-4-((phenylethynyl)sulfonyl)benzene 
• 60682-95-3 1-(diethoxyphosphorylmethylsulfonyl)-4-methylbenzene 
• 37891-95-5 bromomethyl 4-tolyl sulfone 

Downstream Products

• 204389-35-5 (E)-4-methylphenyl 1-deuterio-2-phenylethenyl sulfone 
• 42790-87-4 1-methyl-4-{[(1E)-1-phenylprop-1-en-2-yl]sulfonyl}benzene 
• 105465-60-9 1-((E)-1,3-Diphenyl-prop-1-ene-2-sulfonyl)-4-methyl-benzene 
• 105465-50-7 1-[1-Phenyl-2-(toluene-4-sulfonyl)-propyl]-pyrrolidine 
• 105465-51-8 1-[1,3-Diphenyl-2-(toluene-4-sulfonyl)-propyl]-pyrrolidine 
• 1239456-71-3 (E)-N-(2-methyl-1,3-diphenylprop-2-enyl)-4-methylphenylsulfonamide 
• 70197-09-0 N-(1-phenylpropyl)-4-toluenesulfonamide 
• 4874-85-5 1,5-diphenyl-1H-1,2,3-triazole 
• 1380035-46-0 C₂₂H₂₂O₂S 

Relevant academic research and scientific papers

PHOTODECOMPOSITION OF SELENOSULFONATES AND THEIR FACILE PHOTOADDITION TO ALKENES1

Phenyl areneselenosulfonates (1) are very photosensitive and easily undergo photodecomposition via initial homolysis of the Se-S bond.In the presence alkenes this facile photodissociation of 1 can be used to initiate a free radical chain reaction (eq 6) that leads to addition of 1 to the alkene to form β-phenylselenosulfones (2).The photoaddition requires much shorter reaction times than the non-photolytic addition of 1 to alkenes described recently.

Radical Heck-type reaction of styrenes with sulfonyl hydrazides on water at room temperature

Herein, metal-free radical Heck-type reaction of styrenes with sulfonyl hydrazides to synthesize vinyl sulfones is developed. The reaction is performed under economical TBAI/TBHP system on water in open air at room temperature, which proceeds through the

Alkyne-based, highly stereo- and regioselective synthesis of stereodefined functionalized vinyl tellurides

(Z)-β-Aryltellurovinylphosphonates and (Z)-β-aryltellurovinyl sulfones were synthesized via the highly stereoselective anti-hydrotelluration of 1-alkynylphosphonates and 1-alkynyl sulfones. The configurations of these compounds were characterized via sup

Photocatalytic radical cyclization of α-halo hydrazones with β-ketocarbonyls: Facile access to substituted dihydropyrazoles

A mild and efficient method for the photocatalytic radical cyclization of α-halo hydrazones with β-ketocarbonyls has been described. This strategy provides a potential protocol for the construction of functionalized 4,5-dihydropyrazoles in moderate to high yields.

One-pot approach for the regioselective synthesis of β-keto sulfones based on acid-catalyzed reaction of sulfonyl chlorides with arylacetylenes and water

Reaction of sulfonyl chlorides with arylacetylenes and water in the presence of a catalytic amount of sulfonic acid in THF provided β-keto sulfones in good yields with excellent regioselectivity.

Pd-Catalyzed desulfitative arylation of olefins by: N -methoxysulfonamide

A novel Pd-catalyzed protocol for the desulfitative Heck-type reaction of N-methoxy aryl sulfonamides with alkenes was reported. The cross-coupling reaction was performed successfully with a variety of olefins to obtain aryl alkenes. Different substituents on the aromatic ring of N-methoxysulfonamides were also found to be compatible with the reaction conditions. Expectedly, the reaction proceeds through CuCl2-promoted generation of the nitrogen radical and subsequent desulfonylation under thermal conditions to afford the aryl radical for the Pd-catalyzed coupling reaction. N-Methoxysulfonamide was further exploited for the synthesis of symmetrical biaryls in the presence of CuCl2. This journal is

The Sulfinylsulfonation of alkynes for β-Sulfinyl alkenylsulfone

Here we report the sulfinylsulfonation of alkynes to afford β-sulfinyl alkenylsulfone products with a broad substrate scope, excellent functional group compatibility, and high yield. Moreover, the sulfinylsulfonation reaction of enyne can also be realized for constructing functionalized carbo- and heterocycles through a radical cascade cyclization process.

Visible-light-induced surfactant-promoted sulfonylation of alkenes and alkynes with sulfonyl chloride by the formation of an EDA-complex with NaI in water at room temperature

A green and efficient visible-light-induced iodosulfonyl reaction of alkenes in water using an EDA complex strategy at room temperature has been disclosed. The addition of a cationic surfactant allows for the easy formation of colored EDA complexes in water. The hydrophobic effect of the core in the surfactant aggregates, which act as a reaction medium formed by the surfactants themselves in water, plays a significant role in stabilizing the transition state and decreasing the activation energy of the reaction. Remarkably, transition-metal catalysts and organic solvents were not required in this transformation. Moreover, it displayed a broad substrate scope, good functional group tolerance, simple operation, scalability and high chemical selectivity. Thus, it not only provided a green and efficient synthetic strategy for the preparation of β-iodo-substituted sulfone derivatives, but also enriched the investigation of visible-light-induced reactions in water.

Sulfonylation of Aryl Halides by Visible Light/Copper Catalysis

An efficient visible-light-assisted, copper-catalyzed sulfonylation of aryl halides with sulfinates is reported. In our protocol, a single ligand CuI photocatalyst formed in situ was used in the photocatalytic transformation. Diverse organosulfones were obtained in moderate to good yields. This strategy demonstrates a promising approach toward the synthesis of diverse and useful organosulfones.

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).