Selective continuous flow synthesis of hydroxy lactones from alkenoic acids

Cerra, Bruno; Mangiavacchi, Francesca; Santi, Claudio; Lozza, Anna Maria; Gioiello, Antimo

doi:10.1039/c7re00083a

Cited by 20 publications

(8 citation statements)

References 41 publications

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“…In 2017 [ 119 ], the first study using a selenium-mediated catalysis conducted under flow conditions ( Scheme 42 ) was reported. Lactone rings and their precursors are often found in natural and bioactive compounds.…”

Section: Application Of Non-conventional Energy Sources In Organosele...mentioning

confidence: 99%

“Green Is the Color”: An Update on Ecofriendly Aspects of Organoselenium Chemistry

et al. 2022

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Organoselenium compounds have been successfully applied in biological, medicinal and material sciences, as well as a powerful tool for modern organic synthesis, attracting the attention of the scientific community. This great success is mainly due to the breaking of paradigm demonstrated by innumerous works, that the selenium compounds were toxic and would have a potential impact on the environment. In this update review, we highlight the relevance of these compounds in several fields of research as well as the possibility to synthesize them through more environmentally sustainable methodologies, involving catalytic processes, flow chemistry, electrosynthesis, as well as by the use of alternative energy sources, including mechanochemical, photochemistry, sonochemical and microwave irradiation.

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Section: Application Of Non-conventional Energy Sources In Organosele...mentioning

confidence: 99%

“Green Is the Color”: An Update on Ecofriendly Aspects of Organoselenium Chemistry

et al. 2022

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“…Oxidations by H2O2 benefit from the presence of a catalyst and for this purpose organoselenides have proved particularly convenient. The combination of selenium and hydrogen peroxide is an efficient approach to different important classes of organic reactions, to which Bayer-Villiger oxidations of carbonylated substrates, i.e., aldehydes and ketones, oxidations of alcohols and nitrogen containing compounds and alkene epoxidations belong [1][2][3][4][5][6][7][8]. In the last decade, examples of this catalysis have been reported also in water, paving the route to the use of selenium in green chemistry and moving further apart from the use of toxic heavy metal compounds, like dichromates and permanganates [9,10].…”

Section: H2o2 Reduction By Organoselenidesmentioning

confidence: 99%

Selenium-Catalyzed Reduction of Hydroperoxides in Chemistry and Biology

Orian

Flohé

2021

Antioxidants

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Among the chalcogens, selenium is the key element for catalyzed H2O2 reduction. In organic synthesis, catalytic amounts of organo mono- and di-selenides are largely used in different classes of oxidations, in which H2O2 alone is poorly efficient. Biological hydroperoxide metabolism is dominated by peroxidases and thioredoxin reductases, which balance hydroperoxide challenge and contribute to redox regulation. When their selenocysteine is replaced by cysteine, the cellular antioxidant defense system is impaired. Finally, classes of organoselenides have been synthesized with the aim of mimicking the biological strategy of glutathione peroxidases, but their therapeutic application has so far been limited. Moreover, their therapeutic use may be doubted, because H2O2 is not only toxic but also serves as an important messenger. Therefore, over-optimization of H2O2 reduction may lead to unexpected disturbances of metabolic regulation. Common to all these systems is the nucleophilic attack of selenium to one oxygen of the peroxide bond promoting its disruption. In this contribution, we revisit selected examples from chemistry and biology, and, by using results from accurate quantum mechanical modelling, we provide an accurate unified picture of selenium’s capacity of reducing hydroperoxides. There is clear evidence that the selenoenzymes remain superior in terms of catalytic efficiency.

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“…As part of our ongoing efforts to ameliorate synthetic procedures also using nonconventional technologies [13][14][15][16][17][18] to enable them to meet the principles of green chemistry, and intrigued by the manifold biological activities exerted by xanthines [4], we sought to develop a flexible synthetic procedure intended to improve caffeine synthesis from a green chemistry perspective and, at the same time, prepare a series of diversely N-7 substituted xanthine derivatives. With this aim, we chose to perform these reactions in the Q-tube® apparatus, which allows reactions to be performed under high pressure, overcoming the solvent boiling point and, as a result, increasing the reaction pressure and temperature, thus reducing the reaction time.…”

Section: Introductionmentioning

confidence: 99%

Q-Tube®-Assisted Alkylation and Arylation of Xanthines and Other N-H-Containing Heterocycles in Water

et al. 2021

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In this paper, a simple and clean process for the alkylation and arylation of nitrogen-containing heterocycles is reported. The reactions were conducted using the Q-tube® as a non-conventional technology, in water as a green solvent, at overboiling temperature. The developed strategy was used to improve two steps in the total synthesis of caffeine, as reported by Narayan, and then extended to the preparation of N-decorated xanthines. Finally, piperidine, methyl piperazine, and isatine were proven to be suitable substrates for the protocol proposed herein.

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Selective continuous flow synthesis of hydroxy lactones from alkenoic acids

Abstract: The first in-flow selenium-mediated catalysis has been realized under eco-friendly conditions to convert alkenoic acids into hydroxy lactones with a high regio- and diastereo-selectivity ratio.

Cited by 20 publications

References 41 publications

“Green Is the Color”: An Update on Ecofriendly Aspects of Organoselenium Chemistry

“Green Is the Color”: An Update on Ecofriendly Aspects of Organoselenium Chemistry

Selenium-Catalyzed Reduction of Hydroperoxides in Chemistry and Biology

Q-Tube®-Assisted Alkylation and Arylation of Xanthines and Other N-H-Containing Heterocycles in Water

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