200262-60-8

Upstream product

• 10439-23-3 4-methylbenzenesulfinyl chloride 
• 104-54-1 3-Phenylpropenol 
• 38622-91-2 [(p-methylphenyl)sulfonylmethyl]isonitrile 
• 536-57-2 p-toluene sulfinic acid 
• 824-79-3 sodium 4-methylbenzenesulfinate 
• 100-52-7 benzaldehyde 
• 4393-06-0 1-Phenyl-2-propen-1-ol 

Downstream Products

• 77825-80-0 (E)-1-Phenyl-1-(p-toluenesulfonyl)propene 
• 686304-96-1 (E)-(1-phenylprop-1-enylsulfonyl)benzene 

Relevant academic research and scientific papers

Bismuth(III) bromide-catalysed substitution of benzyl alcohols with arylsulfonylmethyl isocyanides: An unexpected access to sulfinates

A bismuth(III) bromide-catalysed direct substitution of benzyl alcohols with arylsulfonylmethyl isocyanides affords sulfinates under mild acidic conditions. An unforeseen reversed reactivity was observed in this highly selective formation of sulfinates instead of the formation of the usually favoured sulfones. Cytotoxicity tests (in vitro) indicated that the sulfinates exhibit antibiotic activity against a human leukaemia cell line HL-60, which would widen the structural diversity of this antitumour target and confirm the perspectives of further investigations.

Isocyanide-Induced Esterification of Sulfinic Acids to Access Sulfinates

The isocyanide-induced esterification of sulfinic acids with alcohols or thiophenols access to sulfinates has been developed. Various primary, secondary, and tertiary alcohols could be compatible with the established protocols. Notably, such an isocyanide-induced synthetic strategy presented the advantages of simple operation, good functional group tolerance, and more than 40 examples up to 99% yields. (Figure presented.).

Substrate- and temperature-controlled divergence in reactions of alcohols with TosMIC catalyzed by BF3 · Et2O: Facile access to sulfinates and sulfones

An efficient BF3 · Et2O-catalyzed divergent synthesis of sulfinate esters and sulfones through C–O and C–S bond formation has been achieved from alcohols and p-toluenesulfonylmethyl isocyanide (TosMIC). Various alcohols reacted smoothly with TosMIC under the present conditions at room temperature providing sulfinate esters exclusively. By tuning the reaction temperature, the alcohols that provide highly stabilized carbocation in the reaction medium afforded sulfones as sole products. This study was aimed at understanding the regioselectivity of ambidentate sulfinate ion and to elucidate the interpretation of sulfinate/sulfone scaffolds.

Sulfination of Alcohols with p-Toluenesulfonylmethyl Isocyanide under Metal-Free Conditions: A Mitsunobu Approach

A Mitsunobu approach for the synthesis of sulfinate esters by direct nucleophilic substitution of alcohols is described. The salient features of this strategy include neutral and metal-free conditions for the rapid synthesis of sulfinates in high yields. The present protocol using p-toluenesulfonylmethyl isocyanide (TosMIC) and the triphenylphosphine (TPP)/diisopropyl azodicarboxylate (DIAD) reagent system represents the general synthetic route to this important class of compounds. (Figure presented.).

Sulfination of alcohols with sodium sulfinates promoted by BF3·OEt2: An unexpected access

A BF3·OEt2-promoted direct substitution of various alcohols with sodium sulfinates affording sulfinates under mild conditions has been developed. Further reaction of the hydroxysteroids achieves the highly complex sulfinates in good yields, which are two potential pharmacophores routinely encountered in drug discovery.

Tandem Ir-catalyzed allylic substitution reaction of allyl sulfinates and isomerization

(Chemical Equation Presented) An efficient method for the synthesis of trisubstituted vinyl sulfones is reported. Using the [lr(COD)Cl] 2/phosphoramidite ligand (L1)/DBU, trisubstituted vinyl sulfones could be synthesized from allyl sulfinates