23730-30-5

Upstream product

• 536-57-2 p-toluene sulfinic acid 
• 98-85-1 1-Phenylethanol 
• 824-79-3 sodium 4-methylbenzenesulfinate 
• 38622-91-2 [(p-methylphenyl)sulfonylmethyl]isonitrile 

Downstream Products

• 98-85-1 1-Phenylethanol 
• 33895-88-4 4-methyl-4-(toluene-4-sulfonyl)-pentan-2-one 
• 672-65-1 (1-chloroethyl)benzene 
• 32884-74-5 3-[(4-methylphenyl)sulfanyl]-1H-indole 
• 2943-42-2 di(4-methyl)phenylthiosulfonate 
• 98-86-2 acetophenone 
• 100-42-5 styrene 
• 98-59-9 p-toluenesulfonyl chloride 
• 536-57-2 p-toluene sulfinic acid 
• 24422-77-3 1-methyl-4-[(1-phenylethyl)sulfonyl]benzene 

Relevant academic research and scientific papers

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.).

N - P -Toluenesulfinylimidazole: A New in situ Reagent for the Mild and Efficient Synthesis of p -Toluenesulfinate Alkyl Esters and Aryl Esters

A new synthetic methodology has been developed for the synthesis of sulfinate alkyl and aryl esters. The methodology involves the combination of p -toluenesulfinic acid and 1,1′-carbonyldiimidazole (CDI) to create the putative reagent sulfinylimidazole. The process spontaneously releases carbon dioxide upon the addition of the CDI to the acid suggesting the rapid formation of the proposed reagent. Reaction of this reagent with a series of alcohols (primary, secondary, and tertiary) afforded the corresponding sulfinate alkyl esters in good to excellent yields by the addition of alcohols. It was also possible to form the related sulfinate aryl esters by treating the proposed sulfinylimidazole with selected phenols (phenol, p - tert -butylphenol, and thymol). The aryl esters were formed in excellent conversion based on analysis of the 500 MHz 1H NMR spectra of the crude reaction mixtures.

Sodium Arenesulfinates-Involved Sulfinate Synthesis Revisited: Improved Synthesis and Revised Reaction Mechanism

Reaction of alcohols with sodium arenesulfinates could afford either sulfones or sulfinates, and O-attack of sulfinate anions onto the in situ generated carbocation intermediates from alcohols was the previous proposed reaction mechanism in many syntheses of sulfinates. This concept, which is often used consciously or unconsciously, was revised herein by using isotopic labeling experiments and development of an improved sulfinate synthesis. The improved sulfinate synthetic protocol possesses many advantages such as a high sulfinate/sulfone selectivity, a broad substrate scope, metal-free, and mild reaction conditions. The revised reaction mechanism necessitates revision of many previous proposed reaction mechanisms in literatures.

A mixed anhydride approach to the preparation of sulfinate esters and allylic sulfones: Trimethylacetic p-toluenesulfinic anhydride

A reagent combination of toluenesulfinic acid and trimethylacetyl chloride affords a putative trimethylacetic p-toluenesulfinic anhydride. This reagent has been used to prepare a series of sulfinate esters from primary and secondary alcohols. In addition, the reagent was used to convert Baylis-Hillman substrates into allylic sulfones. Attempts to use the reagent to convert amines to sulfinamides were unsuccessful. In contrast, the use of 2-pyrrolidinone afforded N-p-toluenesulfinyl pyrrolidinone in 64% yield. The use of a chiral 4-benzyl-1,3-oxazolidinone or 4-benzyl-1,3-oxazolidine-2-thione led to the isolation of S-p-tolyl p-toluenethiosulfonate.

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 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.

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.