138336-33-1

Upstream product

• 63006-68-8 tert-butyl (phenylthio)acetate 
• 1360789-21-4 2-(phenylsulfonyl)-1-(2,2,6,6-tetramethylpiperidin-1-yl)ethanone 
• 75-65-0 tert-butyl alcohol 
• 3959-23-7 benzenesulfonylacetic acid 
• 5292-43-3 bromoacetic acid tert-butyl ester 
• 38111-44-3 phenylzinc(II) bromide 
• 98-80-6 phenylboronic acid 
• 873-55-2 sodium benzenesulfonate 
• 35059-50-8 t-butyl diazoacetate 
• 108-98-5 thiophenol 

Downstream Products

• 138336-34-2 (1R,1α,3α)-6,6-Dimethyl-4-<2-tert-butoxy-2-oxo-1-(phenylsulfonyl)ethyl>-3-oxabicyclo<3.1.0>hexan-2-one 
• 1578219-95-0 di-tertbutyl 2-(phenylsulfonyl)pentanedioate 
• 1578219-50-7 3-(phenylsulfonyl)dihydro-2H-pyran-2,6(3H)-dione 

Relevant academic research and scientific papers

Method for preparing beta-carbonyl sulfone

The invention discloses a method for preparing beta-carbonyl sulfone. The preparation method comprises the following steps: by taking an alpha-carbonyl diazo compound and sodium arylsulfinate as reaction substrates, cheap silver nitrate as an optimal catalyst, 1, 10-phenanthroline as a ligand and potassium persulfate as an oxidant, carrying out coupling reaction in a mixed solvent of acetonitrileand water to obtain the beta-carbonyl sulfone compound. Compared with the prior art, the method has the advantages of wide reaction substrate range, short reaction time, high reaction yield, mild reaction conditions and the like. Non-toxic and harmless reagents are used as reaction raw materials, so that the method is harmless to the environment and meets the requirements of modern green chemicaldevelopment. Post-reaction treatment is simple, and separation and purification are facilitated. In addition, the reaction can realize gram-scale synthesis, and lays a foundation for practical application.

Nickel(II)-Catalyzed Synthesis of Sulfinates from Aryl and Heteroaryl Boronic Acids and the Sulfur Dioxide Surrogate DABSO

We report a redox-neutral Ni(II)-catalyzed sulfination of readily available aryl and heteroaryl boronic acids. Using the combination of commercially available, air-stable NiBr2·(glyme), a commercially available phenanthroline ligand, and DABSO, boronic acids are efficiently converted to the corresponding sulfinate salts, which can be further elaborated to valuable sulfonyl-containing groups, including sulfones, sulfonamides, sulfonyl fluorides, and sulfonate esters. The catalyst loading can be reduced to 2.5 mol ?% on a gram scale. This practically simple protocol tolerates an unprecedented range of pharmaceutically relevant and electron-poor (hetero)aryl boronic acids, allowing the direct synthesis of active pharmaceutical ingredients.

Pd(NHC)-catalyzed alkylsulfonylation of boronic acids: A general and efficient approach for sulfone synthesis

Robust N-heterocyclic carbene palladium complexes are highly efficient catalysts for direct alkylsulfonylation of (hetero)aryl- or alkenyl-boronic acids with potassium metabisulfite and (hetero)alkyl-halides. Among them, acenaphthoimidazolylidene palladium(ii) complexes exhibited the highest activities, and up to quantitative yields were obtained for diverse structurally distinct sulfones under very mild reaction conditions.

Copper(i)-catalyzed sulfonylative Suzuki-Miyaura cross-coupling

Using a simple copper(i) catalyst has allowed a high yielding sulfonylative-Suzuki-Miyaura cross-coupling reaction to be developed. The process provides a single step route to diaryl sulfones from the direct combination of aryl boronic acids, sulfur dioxide and aryl iodides, and represents the first sulfonylative variant of a classic cross-coupling reaction. Sulfur dioxide is delivered from the surrogate reagent, DABSO. Variation of the reaction conditions allowed interruption of the sulfonylative-Suzuki coupling, resulting in the formation of a presumed Cu-sulfinate intermediate. These sulfinates could be trapped as their sodium salts and treated with electrophiles to allow access to arylalkyl sulfones, β-hydroxyl sulfones, sulfonamides and sulfonyl fluorides.

Acenaphthoimidazolylidene Gold Complex-Catalyzed Alkylsulfonylation of Boronic Acids by Potassium Metabisulfite and Alkyl Halides: A Direct and Robust Protocol to Access Sulfones

A robust acenaphthoimidazolylidene gold complex is demonstrated as a highly efficient catalyst in the direct alkylsulfonylation of boronic acids. Remarkably, a wide range of highly reactive and unreactive C-electrophiles were well-tolerated to produce various (hetero)aryl-alkyl, aryl-alkenyl, and alkenyl-alkyl sulfones in satisfactory yields with 5 mol % catalyst loading. Along with the steric properties of NHC ligands, the high catalytic activity of this gold complex suggests that the strong σ-donation of acenaphthoimidazolylidene also played a role in promoting this challenging redox-neutral catalytic process.

Palladium(II)-Catalyzed Synthesis of Sulfinates from Boronic Acids and DABSO: A Redox-Neutral, Phosphine-Free Transformation

A redox-neutral palladium(II)-catalyzed conversion of aryl, heteroaryl, and alkenyl boronic acids into sulfinate intermediates, and onwards to sulfones and sulfonamides, has been realized. A simple Pd(OAc)2 catalyst, in combination with the sulfur dioxide surrogate 1,4-diazabicyclo[2.2.2]octane bis(sulfur dioxide) (DABSO), is sufficient to achieve rapid and high-yielding conversion of the boronic acids into the corresponding sulfinates. Addition of C- or N-based electrophiles then allows conversion into sulfones and sulfonamides, respectively, in a one-pot, two-step process.

Diastereoselective synthesis of γ- And δ-lactams from imines and sulfone-substituted anhydrides

Sulfone-substituted γ- and δ-lactams have been prepared in a single step with high diastereoselectivity. Sulfonylglutaric anhydrides produce intermediates that readily decarboxylate to provide δ-lactams with high diastereoselectivity. Substituents at the 3- or 4-position of the glutaric anhydride induce high levels of stereocontrol. Sulfonylsuccinic anhydrides produce intermediate carboxylic acids that can be trapped as methyl esters or allowed to decarboxylate under mild conditions. This method has been applied to a short synthesis of the pyrrolizidine alkaloid (±)-isoretronecanol.

Synthesis of sulfones from organozinc reagents, DABSO, and alkyl halides

Organozinc reagents react with the SO2 surrogate DABSO, and the resulting zinc sulfinate salts are alkylated in situ to afford sulfones. This transformation has a broad scope and is compatible with a wide range of structural motifs of medicinal

Switching pathways: Room-temperature neutral solvolysis and substitution of amides

Stick or twist: By introducing steric hindrance at the nitrogen atom, stable linear amides bearing an electron-withdrawing α-substituent (Z=Ar, PhSO2, P(O)(OR)2, CN, or CO2R) can be induced to undergo solvolysis and substitution reactions through an elimination-addition mechanism (see picture). Key to this process is a low barrier to rotation around the amide bond and the α-substituentZ. Copyright

Solid state oxidation of aromatic sulfides to corresponding phenyl and p-tolyl sulfoxides and sulone using oxone

Phenyl and p-tolyl sulfides 1 can be selectively oxidised to the corresponding sulfoxides 2 or sulfones 3 in solid state condition using oxone. The advantages of this method are the use of cheap and safe reagents, high yield and simple operating conditions.