Assessing photochemistry as a green synthetic method. Carbon–carbon bond forming reactions

Protti, Stefano; Dondi, Daniele; Fagnoni, Maurizio; Albini, Angelo

doi:10.1039/b810594d

Cited by 59 publications

(49 citation statements)

References 65 publications

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“…According to conventional wisdom, a photochemical reaction should be carried out under a diluted solution to ensure a high efficiency . Moreover, ARS in ARS‐TiO 2 preferred a diluted condition to avoid the aggregation‐caused weakening or quenching of fluorescence of ARS at high concentrations.…”

Section: Resultscontrasting

confidence: 53%

“…3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 According to conventional wisdom, a photochemical reaction should be carried out under a diluted solution to ensure a high efficiency. [32] Moreover, ARS in ARS-TiO 2 preferred a diluted condition to avoid the aggregation-caused weakening or quenching of fluorescence of ARS at high concentrations.…”

Section: Resultsmentioning

confidence: 99%

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Improving the Visible Light Photocatalytic Aerobic Oxidation of Sulfides into Sulfoxides on Dye‐Sensitized TiO₂

et al. 2018

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Visible light‐driven interfacial redox reactions during dye‐sensitized TiO2 are essential to meet the energy and environmental challenges in the form of dye‐sensitized solar cells and sensitized degradation of organic pollutants. Inspired by these prior successes, it is conceivable that the underlying principles of these processes can guide us to construct selective chemical transformations in which the control of selectivity is in higher demand. We attempt to improve the selectivity for sulfoxides during the visible light‐driven selective aerobic oxidation of sulfides in the merger of dye‐sensitized TiO2 photocatalysis with TEMPO [(2,2,6,6‐tetramethylpiperidin‐1‐yl)oxyl] catalysis. Thus, different factors like the TEMPO and its derivatives, initial O2 pressures, initial sulfide concentrations, solvents, light‐emitting diodes (LED) and TiO2 were examined to identify the critical factor for selectivity improvement. It was found that an easily synthesized anatase TiO2, sensitized by 0.33 mol % of alizarin red S, was significant in improving the selectivity for sulfoxides at high conversions of sulfides with the aid of 2 mol % of TEMPO as a redox mediator under blue LED irradiation. This work suggests that the engineering of the TiO2 materials can be a viable solution in improving the selectivity of visible light‐driven chemical transformations by dye‐sensitized TiO2 photocatalysis.

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Section: Resultscontrasting

confidence: 53%

Section: Resultsmentioning

confidence: 99%

Improving the Visible Light Photocatalytic Aerobic Oxidation of Sulfides into Sulfoxides on Dye‐Sensitized TiO₂

et al. 2018

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“…Si−H activation in trisubstituted silanes takes place under mild conditions and does not require any toxic (e.g., tin hydrides), expensive, or potentially explosive (e.g., peroxides) initiators to promote the process and can be performed easily under continuous‐flow conditions. Moreover, the capability of the photocatalyst to absorb in the UV‐A region allows the use of sunlight to perform the desired hydrosilylation, with no need to waste energy for the operation of a lamp, which makes the process green . Aromatic tertiary silanes give clean hydrosilylation reactions with satisfactory to good yields, whereas less reactive aliphatic derivatives give mainly mixtures in which the product distribution is dependent on the structure of the olefin.…”

Section: Resultsmentioning

confidence: 99%

“…Moreover,t he capability of the photocatalystt oa bsorb in the UV-A region [27] allows the use of sunlight to performt he desired hydrosilylation, with no need to waste energy for the operation of al amp, which makes the process green. [43] Aromatic tertiarys ilanes give clean hydrosilylation reactions with satisfactory to good yields, whereas less reactive aliphatic derivatives give mainly mixtures in which the product distribution is dependento nt he structure of the olefin.…”

Section: Discussionmentioning

confidence: 99%

Decatungstate‐Photocatalyzed Si−H/C−H Activation in Silyl Hydrides: Hydrosilylation of Electron‐Poor Alkenes

et al. 2015

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Tetrabutylammonium decatungstate has been used for the photocatalytic activation of the Si−H bond in trisubstituted silanes and applied for the hydrosilylation of electron‐poor alkenes. The mechanism that occurs depends on the silyl hydride used, as supported by laser flash photolysis and EPR trapping experiments. Homolytic Si−H cleavage through a hydrogen atom transfer from the silane to the excited catalyst operates with dimethylphenylsilane and methyldiphenylsilane, for which the hydrosilylation yields were satisfactory. If we used tertiary silanes that have more labile Si−H bonds, such as triphenylsilane or tris(trimethylsilyl)silane, the reaction worked to some extent even under uncatalyzed conditions because of a radical chain reaction. Competition between C−H and Si−H cleavage was observed, however, if we used trialkylsilanes (e.g., triethylsilane). In favorable cases, the process was also efficient under flow conditions or if promoted by sunlight.

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“…E-factor and material efficiency (ME) have been selected to evaluate the greenness of the synthetic procedures. E-factor is a very useful metric tool that is defined as E-Factor = mass of wastes/mass of product [29,30]. The E-factor can be used to calculate the material efficiency of the process according to the equation: ME = 1/E-factor +1 [30].…”

Section: General Proceduresmentioning

confidence: 99%

Synthesis and Biological Evaluation of New 1,3-Thiazolidine-4-one Derivatives of 2-(4-Isobutylphenyl)propionic Acid

et al. 2014

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New thiazolidine-4-one derivatives of 2-(4-isobutylphenyl)propionic acid (ibuprofen) have been synthesized as potential anti-inflammatory drugs. The structure of the new compounds was proved using spectral methods (FR-IR, 1 H-NMR, 13 C-NMR, MS). The in vitro antioxidant potential of the synthesized compounds was evaluated according to the total antioxidant activity, the DPPH and ABTS radical scavenging assays. Reactive oxygen species (ROS) and free radicals are considered to be involved in many pathological events like diabetes mellitus, neurodegenerative diseases, cancer, infections and more recently, in inflammation. It is known that overproduction of free radicals may initiate and amplify the inflammatory process via upregulation of genes involved in the production of proinflammatory cytokines and adhesion molecules. The chemical modulation of acyl hydrazones of ibuprofen 3a-l through cyclization to the corresponding thiazolidine-4-ones 4a-n led to increased antioxidant potential, as all thiazolidine-4-ones were more active than their parent acyl hydrazones and also ibuprofen. The most active compounds are the thiazolidine-4-ones 4e, m, which showed the highest DPPH radical scavenging ability, their activity being comparable with vitamin E.

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Assessing photochemistry as a green synthetic method. Carbon–carbon bond forming reactions

Cited by 59 publications

References 65 publications

Improving the Visible Light Photocatalytic Aerobic Oxidation of Sulfides into Sulfoxides on Dye‐Sensitized TiO₂

Improving the Visible Light Photocatalytic Aerobic Oxidation of Sulfides into Sulfoxides on Dye‐Sensitized TiO₂

Decatungstate‐Photocatalyzed Si−H/C−H Activation in Silyl Hydrides: Hydrosilylation of Electron‐Poor Alkenes

Synthesis and Biological Evaluation of New 1,3-Thiazolidine-4-one Derivatives of 2-(4-Isobutylphenyl)propionic Acid

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Assessing photochemistry as a green synthetic method. Carbon–carbon bond forming reactions

Cited by 59 publications

References 65 publications

Improving the Visible Light Photocatalytic Aerobic Oxidation of Sulfides into Sulfoxides on Dye‐Sensitized TiO2

Improving the Visible Light Photocatalytic Aerobic Oxidation of Sulfides into Sulfoxides on Dye‐Sensitized TiO2

Decatungstate‐Photocatalyzed Si−H/C−H Activation in Silyl Hydrides: Hydrosilylation of Electron‐Poor Alkenes

Synthesis and Biological Evaluation of New 1,3-Thiazolidine-4-one Derivatives of 2-(4-Isobutylphenyl)propionic Acid

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Improving the Visible Light Photocatalytic Aerobic Oxidation of Sulfides into Sulfoxides on Dye‐Sensitized TiO₂

Improving the Visible Light Photocatalytic Aerobic Oxidation of Sulfides into Sulfoxides on Dye‐Sensitized TiO₂