“On water” reactivity between carbohydrate-derived nitroalkenes and furans

Luque-Agudo, Verónica; Gil, M.V.; Román, Emilio; Serrano, José Antonio

doi:10.1039/c6gc00555a

Cited by 16 publications

(5 citation statements)

References 41 publications

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“…The impact of the hydrophobic hydration effect on enantioselectivity is further enhanced by decreasing droplet size, which can be achieved by accelerated stirring. Proper magnetic stirring has been known to increase the interfacial area and hence, the hydrogen bonding networks align more efficiently; 107 the higher the stirring rate the lower the droplet size in the emulsion. Rates of stirring at 200, 600, and 1150 rpm were tested, with maximum ee being reached at 1150 rpm for all six substrates.…”

Section: Applicationsmentioning

confidence: 99%

Water as the reaction medium in organic chemistry: from our worst enemy to our best friend

et al. 2021

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Section: Applicationsmentioning

confidence: 99%

Water as the reaction medium in organic chemistry: from our worst enemy to our best friend

et al. 2021

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“…Further insights into the on-water acceleration phenomenon were obtained by studying the impact of mixing speed on the reaction mixture, inspired by prior works 43 – 45 . The lack of stirring led to sluggish progression due to poor mass transfer, yielding only 13% conversion of 3aa [ exo + endo ] in 2 h. With very gentle stirring at 200 rpm, a slight increase in the product conversion was observed (23% of 3aa [ exo + endo ], 2 h).…”

Section: Resultsmentioning

confidence: 99%

“On-Water” accelerated dearomative cycloaddition via aquaphotocatalysis

Kim,

Bae

2024

Nat Commun

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Sulfur(VI) fluoride exchange (SuFEx) has emerged as an innovative click chemistry to harness the pivotal connectivity of sulfonyl fluorides. Synthesizing such alkylated S(VI) molecules through a straightforward process is of paramount importance, and their water-compatibility opens the door to a plethora of applications in biorelevant and materials chemistry. Prior aquatic endeavors have primarily focused on delivering catalysts involving ionic mechanisms, studies regarding visible-light photocatalytic transformation are unprecedented. Herein we report an on-water accelerated dearomative aquaphotocatalysis for heterocyclic alkyl SuFEx hubs. Notably, water exerts a pronounced accelerating effect on the [2 + 2] cycloaddition between (hetero)arylated ethenesulfonyl fluorides and inert heteroaromatics. This phenomenon is likely due to the high-pressure-like reactivity amplification at the water-oil interface. Conventional solvents proved totally ineffective, leading to the isomerization of the starting material.

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“…[ 10 ] Recently, many synthetic works have been carried out in the presence of aqueous media. [ 11–15 ]…”

Section: Introductionmentioning

confidence: 99%

“…[10] Recently, many synthetic works have been carried out in the presence of aqueous media. [11][12][13][14][15] There is a metric established for the use of antibiotics by the World Health Organization called DDD (defined daily dose). [16,17] But the strength of this metric is doubtful in hospitalized humans because its measurement is based on human weight.…”

Section: Introductionmentioning

confidence: 99%

An efficient green approach for the synthesis of benzothiazole‐linked pyranopyrazoles as promising pharmacological agents and docking studies

Reddy

Garcia

Subbaiah

et al. 2021

Journal of Heterocyclic Chem

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Benzothiazole‐tethered pyranopyrazoles derivatives were prepared via environmentally favorable conditions, which included eco‐friendly catalyst, ethanol−water solvent, one‐pot reaction, and atom‐ and step‐economy procedures. Excellent yield of the products was observed. Besides, all products were screened for their antimicrobial behavior. From the biological results, it was seen that most of the compounds possessed high to moderate antimicrobial properties. Compound 6a gave prominent antimicrobial property followed by 6d, 6l, and 6n. In addition, computer‐aided studies of the active compounds were also conducted. In this, selected compounds were docked into the intercalation site of DNA of the DNA−gyrase complex. From these results, the highest binding energy of −10.1 kcal/mol was for 6a against DNA−gyrase. This is the first eco‐friendly synthetic method for the preparation of benzothiazole‐pyranopyrazoles and the synthetic effort in this study may serve as a model for additional environmentally benign reactions. The biological results may prompt further studies related to antibiotic drugs.

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“On water” reactivity between carbohydrate-derived nitroalkenes and furans

Abstract: Eco-friendly “on water” reactions of carbohydrate-derived nitroalkenes with furan, 2-methylfuran and furfural N,N-dimethylhydrazone have been investigated under different mixing methods, such as a magnetic stirrer and a wrist-action shaker.

Cited by 16 publications

References 41 publications

Water as the reaction medium in organic chemistry: from our worst enemy to our best friend

Water as the reaction medium in organic chemistry: from our worst enemy to our best friend

“On-Water” accelerated dearomative cycloaddition via aquaphotocatalysis

An efficient green approach for the synthesis of benzothiazole‐linked pyranopyrazoles as promising pharmacological agents and docking studies

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