Non-expensive, open-flask and selective catalytic systems for the synthesis of sulfinate esters and thiosulfonates

Tranquilino, Arisson; Andrade, S Robles; Silva, Ana Paula M. da; Menezes, Paulo H.; Oliveira, Roberta A.

doi:10.1016/j.tetlet.2017.02.025

Cited by 35 publications

(21 citation statements)

References 46 publications

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“… 87 , 88 Subsequently, the benzenesulfinic acid generated can be converted into 8a in the presence of TBAI. 89 , 90 Finally, a sulfenylation cycle was established.…”

Section: Resultsmentioning

confidence: 99%

Sulfenylation of Arenes with Ethyl Arylsulfinates in Water

Wei

Liu

et al. 2020

ACS Omega

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A tetrabutylammonium iodide-mediated direct sulfenylation of arenes with ethyl arylsulfinates in water was developed. Various electron-rich arenes and ethyl arylsulfinates were investigated in the reaction, and a series of aryl sulfides were obtained in excellent yields. The advantages of this green protocol were simple reaction conditions (metal-free, water as the solvent, and under air), odorless and easily available sulfur reagent, broad substrate scope, and gram-scale synthesis. Moreover, the potential application of aryl sulfides was exemplified by further transformations.

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“… 87 , 88 Subsequently, the benzenesulfinic acid generated can be converted into 8a in the presence of TBAI. 89 , 90 Finally, a sulfenylation cycle was established.…”

Section: Resultsmentioning

confidence: 99%

Sulfenylation of Arenes with Ethyl Arylsulfinates in Water

Wei

Liu

et al. 2020

ACS Omega

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“…There was an interest in exploring the utility of this method in the context of an acid sensitive substrate. There are existing methodologies for the preparation of sulfinate esters that employ conditions that occur in the presence of catalytic sulfuric acid 10 or Lewis acids (e.g., BF 3 •OEt 2 ). 3c,17 and these conditions would not be compatible with such substrates.…”

Section: Table 2 Cdi-mediated Sulfinylation With No Induction Timementioning

confidence: 99%

“…8 There are various other synthetic methods beyond the examples that are mentioned here. [9][10][11] In the search for an improved methodology (ease of preparation and purification, commercially available reagents, and reduced environmentally impact) for the synthesis of sulfinate esters, a new method of sulfinyl group activation was considered. Conceptually, the preparation of sulfinate esters from sulfinic acids would require the formation of a suitable leaving group for the sulfinyl group.…”

mentioning

confidence: 99%

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

Shaw¹,

Austermuehle²,

Witte³

et al. 2021

Synthesis

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A new synthetic methodology has been developed for the synthesis of sulfinate alkyl and aryl esters. The methodology involves the combination of <i>p</i>-toluenesulfinic acid and 1,1’-carbonyl diimidazole (CDI) to create the putative reagent sulfinyl imidazole. 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 yield by the addition of alcohols. It was also possible to form the related sulfinate aryl esters by treating the proposed sulfinyl imidazole with selected phenols (phenol, <i>p</i>-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.

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“…In the field of chalcogen chemistry, Menezes and Freitas have demonstrated how these elements can be applied in the synthesis of (Z)-1,3-enynes pseudoglycosides (Dantas et al 2016) ( Figure 63). The same group, in collaboration with Oliveira, has recently reported two simple and efficient methods for the synthesis of sulfinate esters and thiosulfonates from sodium salts of sulfinic acids (Tranquilino et al 2017).…”

Section: Examples Of Large-scale Complex Synthesesmentioning

confidence: 99%

Organic Synthesis: New Vistas in the Brazilian Landscape

Pilli

Assis

2018

An. Acad. Bras. Ciênc.

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In this overview, we present our analysis of the future of organic synthesis in Brazil, a highly innovative and strategic area of research which underpins our social and economical progress. Several different topics (automation, catalysis, green chemistry, scalability, methodological studies and total syntheses) were considered to hold promise for the future advance of chemical sciences in Brazil. In order to put it in perspective, contributions from Brazilian laboratories were selected by the citations received and importance for the field and were benchmarked against some of the most important results disclosed by authors worldwide. The picture that emerged reveals a thriving area of research, with new generations of well-trained and productive chemists engaged particularly in the areas of green chemistry and catalysis. In order to fulfill the promise of delivering more efficient and sustainable processes, an integration of the academic and industrial research agendas is to be expected. On the other hand, academic research in automation of chemical processes, a well established topic of investigation in industrial settings, has just recently began in Brazil and more academic laboratories are lining up to contribute. All these areas of research are expected to enable the future development of the almost unchartered field of scalability.

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Non-expensive, open-flask and selective catalytic systems for the synthesis of sulfinate esters and thiosulfonates

Cited by 35 publications

References 46 publications

Sulfenylation of Arenes with Ethyl Arylsulfinates in Water

Sulfenylation of Arenes with Ethyl Arylsulfinates in Water

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

Organic Synthesis: New Vistas in the Brazilian Landscape

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