18723-83-6

Upstream product

• 141811-44-1 2-(ethanesulfonyl)acetic acid 
• 100-52-7 benzaldehyde 
• 20875-42-7 1-(ethylthio)-2-phenylethene 
• 108-86-1 bromobenzene 
• 1889-59-4 ethyl vinyl sulfone 
• 96-09-3 styrene oxide 
• 23451-56-1 2-(ethylthio)-1-phenylethanol 
• 5153-67-3 nitrostyrene 
• 20035-08-9 sodium ethanesulfinate 
• 54885-04-0 phenyl(quinolin-8-yl)methanone 
• 140-10-3 (E)-3-phenylacrylic acid 
• 637-44-5 phenylpropyolic acid 
• 103-64-0 bromostyrene 
• 40321-37-7 diethyl ((ethylsulfonyl)methyl)phosphonate 

Downstream Products

• 70624-80-5 1-[(1E)-2-phenylethenyl]-tricyclo[3.3.1.1^3,7]decane 
• 66499-26-1 (2-(ethylsulfonyl)ethyl)benzene 

Relevant academic research and scientific papers

Stereo-recognizing transformation of (E)-alkenyl halides into sulfides catalyzed by nickel(0) triethyl phosphite complex

(E)-Alkenyl halides were transformed into (E)-alkenyl sulfides by the nickel(0) triethyl phosphite complex-catalyzed reaction with thiols, whereas (Z)-alkenyl halides gave alkynes under the same reaction conditions. Aryl halides were also transformed into aryl sulfides using the same reagent system.

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).

Photocatalyst-free visible light driven synthesis of (E)-vinyl sulfones from cinnamic acids and arylazo sulfones

A photocatalyst-free visible light mediated decarboxylative sulfono functionalization protocol has been explored for the synthesis of (E)-vinyl sulfones from cinnamic acids and bench-stable arylazo sulfones. The latter have been utilized as sulfonyl radic

Metal-free synthesis of (E)-vinyl sulfones via denitrative coupling reactions of β-nitrostyrenes with sodium sulfinates

A practical metal-free procedure for the synthesis of (E)-vinyl sulfones has been developed through the coupling of β-nitrostyrenes with sodium sulfinates under microwave irradiation. This methodology provides a convenient and efficient approach to various (E)-vinyl sulfones from readily available starting materials with excellent regioselectivity. The present oxidative reaction involves an efficient denitrative radical cross-coupling of β-nitrostyrenes with sodium sulfinates via using AcOH as an additive.

Oxidative coupling of Michael acceptors with aryl nucleophiles produced through rhodium-catalyzed C-C bond activation

Utilizing rhodium catalysis, aryl nucleophiles generated via carbon-carbon single bond activation successfully undergo oxidative coupling with Michael acceptors. The reaction scope encompasses a broad range of nucleophiles generated from quinolinyl ketones as well as a series of electron deficient terminal alkenes, illustrating the broad potential of intersecting carbon-carbon bond activation with synthetically useful coupling methodologies. The demonstrated oxidative coupling produces a range of cinnamyl derivatives, several of which are challenging to prepare via conventional routes.

Silver-Catalyzed Denitrative Sulfonylation of β-Nitrostyrenes: A Convenient Approach to (E)-Vinyl Sulfones

The first utilization of β-nitrostyrenes (readily available by the Henry reaction) for a highly stereoselective, convenient, and catalytic synthesis of (E)-vinyl sulfones at room temperature was investigated. The protocol involves efficient silver-catalyz

Phosphoric Acid-Mediated Synthesis of Vinyl Sulfones through Decarboxylative Coupling Reactions of Sodium Sulfinates with Phenylpropiolic Acids

A novel phosphoric acid -mediated synthesis of vinyl sulfones through decarboxylative coupling reactions of sodium sulfinates with phenylpropiolic acids is described. This transformation is efficient and environmentally friendly.

Transition-metal-free synthesis of vinyl sulfones via tandem cross-decarboxylative/coupling reactions of sodium sulfinates and cinnamic acids

A transition-metal-free synthesis of vinyl sulfones, utilizing sodium sulfinates and cinnamic acids through tandem cross-decarboxylative/coupling reactions, has been developed. This transformation is simple, efficient and environmentally benign, with a wide range of substrate scope and exceptional functional group tolerance. This journal is the Partner Organisations 2014.

Chemoselective synthesis of unsymmetrical internal alkynes or vinyl sulfones via palladium-catalyzed cross-coupling reaction of sodium sulfinates with alkynes

A highly efficient and mild palladium-catalyzed cross-coupling of sodium sulfinates and alkynes for the selective synthesis of unsymmetrical internal alkynes and vinyl sulfones has been developed. This methodology has advantages of easily accessible starting materials, functional group tolerance and a wide range of substrates, which provides rapid access to alkynes and vinyl sulfones.

Stereoselective heck reactions with vinyl sulfoxides, sulfides and sulfones

We report the Heck cross-coupling of notoriously unreactive, but synthetically valuable olefins: vinyl sulfoxides, vinyl sulfones, and vinyl sulfides. Key findings include the importance of the sterically hindered (tri-tert-butyl)phosphine ligand and the unique effectiveness of triethylamine as the base. The method is general, E-selective, and can be used to synthesize disubstituted or trisubstituted olefins through simple adjustments of stoichiometry. Copyright