26189-65-1

Upstream product

• 77825-71-9 trans-2-(Benzenesulfonyl)-1-(phenylseleno)indan 
• 108-98-5 thiophenol 
• 95-13-6 1-indene 
• 10485-09-3 2-bromoindene 
• 873-55-2 sodium benzenesulfonate 
• 60805-71-2 phenylselenyl benzenesulfonate 
• 1822-73-7 phenylthioethylene 
• 69627-08-3 1-(phenylsulfonyl)-1-(trimethylsilyl)ethene 
• 5535-49-9 2-Chloroethyl phenyl sulfide 
• 62762-20-3 1-phenylthio-1-trimethylsilylethene 
• 524938-08-7 2-[2-phenylsulfonyl-2-(trimethylsilyl)ethyl]benzaldehyde 

Downstream Products

• 74259-46-4 7a-Benzenesulfonyl-1,1,2,2-tetramethyl-2,2a,7,7a-tetrahydro-1H-cyclobuta[a]indene 
• 92-52-4 biphenyl 
• 4505-48-0 2-phenylindene 
• 95-13-6 1-indene 
• 74259-48-6 8b-Benzenesulfonyl-4c,5,6,7,8,8a,8b,9-octahydro-4bH-benzo[3,4]cyclobuta[1,2-a]indene 
• 74259-47-5 8a-Benzenesulfonyl-1,2,3,3a,3b,8,8a,8b-octahydro-cyclopenta[3,4]cyclobuta[1,2-a]indene 

Relevant academic research and scientific papers

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.

Engaging sulfinate salts via Ni/photoredox dual catalysis enables facile Csp2-SO2R coupling

This report details the development and implementation of a strategy to construct aryl- and heteroaryl sulfones via Ni/photoredox dual catalysis. Using aryl sulfinate salts, the C-S bond can be forged at room temperature under base-free conditions. An array of aryl- and heteroaryl halides are compatible with this approach. The broad tolerance and mild nature of the described reaction could potentially be employed to prepare sulfones with biological relevance (e.g., in bioconjugation, drug substance synthesis, etc.) as demonstrated in the synthesis of drug-like compounds or their precursors. When paired with existing Ni/photoredox chemistry for Csp3-Csp2 cross-coupling, an array of diverse sulfone scaffolds can be readily assembled from bifunctional electrophiles. A mechanistic manifold consistent with experimental and computational data is presented.

E -Selective synthesis of vinyl sulfones via silver-catalyzed sulfonylation of styrenes

An efficient and highly E-selective protocol for the synthesis of vinyl sulfones is described. This simple protocol demonstrates the first synthesis of vinyl sulfones via a silver-catalyzed C-S bond coupling reaction. In addition, the success of the reaction was found to be critically dependent on the use of TEMPO as the additive.

New method for the synthesis of indenes

A new two-step method was developed for the synthesis of 2-sulfonyl-substituted indenes from aromatic aldehydes. The reactions of 1-phenylsulfonyl-1-(trimethylsilyl)ethylene with ortho-lithiated derivatives of aromatic and heteroaromatic aldehydes afford conjugate addition products whose subsequent cyclization gives substituted 2-sulfonylindenes in preparative yields. The reactions of 2-(phenylsulfonyl)indenes with Grignard reagents were studied. It was shown that the sulfonyl group can be replaced in the presence of iron(III) acetylacetonate.

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

Selenosulfonation: Boron Trifluoride Catalyzed or Thermal Addition of Selenosulfonates to Olefins. A Novel Regio- and Stereocontrolled Synthesis of Vinyl Sulfones.

Se-Phenyl areneselenosulfonates 1 add to a variety of olefins to produce β-phenylseleno sulfones 2.The reaction may be performed in the presence of boron trifluoride etherate to produce chiefly or exclusively Markovnikov products arising from a stereospecific anti addition.Alternatively, the addition may be thermally induced to afford anti-Markovnikov products generated by a nonstereospecific free-radical process.The two modes of addition achieve complementary regiospecificity.The β-phenylseleno sulfones are converted in high yield to vinyl sulfones by stereospecific oxidation-elimination with m-chloroperbenzoic acid.