23730-26-9

Upstream product

• 536-57-2 p-toluene sulfinic acid 
• 75-65-0 tert-butyl alcohol 
• 10439-23-3 4-methylbenzenesulfinyl chloride 
• 788-86-3 p-tolylsulfinyl p-tolyl sulfone 
• 6873-90-1 N-benzyl-4-methylbenzenesulfinamide 
• 98-59-9 p-toluenesulfonyl chloride 
• 911820-09-2 3-[(4-methylphenyl)sulfinyl]propanoic acid tert-butyl ester 
• 181934-30-5 1-[(triisopropylsilyl)ethynyl]-1,2-benziodoxol-3(1H)-one 
• 88-67-5 2-Iodobenzoic acid 
• 103-19-5 di(p-tolyl) disulfide 
• 75-91-2 tert.-butylhydroperoxide 
• 106-45-6 para-thiocresol 
• 304-91-6 o-iodosobenzoic acid 
• 107474-02-2 1-(triisopropylsilyl)-2-(trimethylsilyl)acetylene 

Downstream Products

• 49833-45-6 tert-butyl 4-methylphenyl sulfoxide 

Relevant academic research and scientific papers

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.

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.).

Metal-Free Electrophilic Alkynylation of Sulfenate Anions with Ethynylbenziodoxolone Reagents

Alkynyl sulfoxides are important building blocks with a unique reactivity in organic chemistry, but only a few reliable methods have been reported to synthesize them. A novel route to access alkynyl sulfoxides is reported herein by using ethynyl benziodoxolone (EBX) reagents to trap sulfenate anions generated in situ, via a retro-Michael reaction. The reaction takes place under metal-free and mild conditions. It is compatible with aryl, heteroaryl, and alkyl sulfoxides with up to 90% yield. This practical access to alkynyl sulfoxides is expected to facilitate the application of these useful building blocks in organic synthesis.

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.

TBHP/TBAI-mediated oxidation of thiophenols for the synthesis of tert-butyl arylsulfinates

A novel and efficient TBHP/TBAI-mediated oxidation of thiophenols is described. The reactions proceeded smoothly to give tert-butyl arylsulfinates in up to 82% yield with good functional group compatibility under mild conditions.

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.).

An efficient and novel method for the synthesis of sulfinate esters under solvent-free conditions

The present letter describes a reliable one-stage process for the preparation of sulfinate esters from the corresponding sulfinic acid and alcohols in the presence of N,N′-dicyclohexylcarbodiimide (DCC) under solvent-free conditions.

An improved and efficient procedure for the preparation of chiral sulfinates from sulfonyl chloride using triphenylphosphine

An improved procedure of the Sharpless method for the preparation of chiral sulfinates by triphenylphosphine is described. A mixture of sulfonyl chlorides and diacetone-D-glucose or l-menthol in the presence of triethylamine was treated with triphenylphos

Hypervalent iodine in synthesis. XXIV: A facile method for the preparation of arylsulfinic esters: Oxidation of disulfides or thiophenols by phenyliodine(III) bis(trifluoroacetate) in the presence of alcohols

Arylsulfinic esters were prepared by the oxidation of diaryl disulfides or thiophenols with phenyliodine(III) bis(trifluoroacetate) in the presence of alcohols.