Organocatalytic Oxidation of Organosilanes to Silanols

Limnios, Dimitris; Kokotos, Christoforos G.

doi:10.1021/cs400515w

Cited by 89 publications

(51 citation statements)

References 53 publications

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“…Pioneering attempts by Adam, Mello, and Curci promote the use of dioxiranes for this transformation, whereas Resnati demonstrates the oxidation of organosilanes by utilizing polyfluorooxaziridine . In 2013, Kokotos and co‐workers proposed an organocatalytic oxidation of organosilanes to silanols by using 2,2,2‐trifluoroacetophenone as the catalyst and H 2 O 2 as the oxidant (Scheme ) …”

Section: Other Oxidation Reactions and Mechanistic Studiesmentioning

confidence: 99%

Green Organocatalytic Oxidative Methods using Activated Ketones

2018

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Alkenes are very important moieties in organic chemistry and have been employed as starting materials for the synthesis of important organic compounds. In this review, we present organocatalytic reactions in which alkenes play a central role, especially their organocatalytic oxidation to epoxides. This topic plays a pivotal role in our recent research, for which we utilize H2O2 as a green oxidant and a ketone as the catalyst. Extension to other oxidative transformations is also presented.

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Section: Other Oxidation Reactions and Mechanistic Studiesmentioning

confidence: 99%

Green Organocatalytic Oxidative Methods using Activated Ketones

2018

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“…Moreover, Limnios and Kokotos have recently reported an environmentally friendly method for the epoxidation of alkenes with 2,2,2‐trifluoroacetophenone as an organocatalyst in combination with a green oxidant – aqueous H 2 O 2 in acetonitrile and tert ‐butyl alcohol 25,26…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Supramolecular Behavior, and In Vitro Photodynamic Activities of Novel Zinc(II) Phthalocyanines “Side‐strapped” with Crown Ether Bridges

Chen¹,

Ke²,

Li³

et al. 2013

Chemistry An Asian Journal

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Two new tetra- or di-α-substituted zinc(II) phthalocyanines 5 and 6 have been prepared through a "side-strapped" method. In the molecules, the adjacent benzene rings of the phthalocyanine core are linked at α-position through a triethylene glycol bridge to form a hybrid aza-/oxa-crown ether. The tetra-α-substituted phthalocyanine 5 shows an eclipsed self-assembly property in CH2Cl2 and the effect on the di-α-substituted analogue 6 is significantly weakened. Furthermore, the crown ethers of these compounds can selectively complex with Fe(3+) or Cu(2+) ion in DMF, leading to formation of J-aggregated nano-assemblies, which can be disaggregated in the presence of some organic or inorganic ligands, such as triethylamine, tetramethylethylenediamine, CH3COO(-), or OH(-). In addition, both compounds are efficient singlet oxygen generators with the singlet oxygen quantum yields (Φ(Δ)) of 0.54-0.74 in DMF relative to unsubstituted zinc(II) phthalocyanine (Φ(Δ)=0.56). They exhibit photodynamic activities toward HepG2 human hepatocarcinoma cells, but the compound 6, which has more than 40-fold lower IC50 value (0.08 μM) compared to the analogue 5 (IC50=3.31 μM), shows remarkablely higher in vitro photocytotoxicity due to its significantly higher cellular uptake and singlet oxygen generation efficiency. The results suggest that these compounds can serve as promising multifunctional materials both in (opto)electronic field and photodynamic therapy.

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“…Previously, 2,2,2‐trifluoacetophenone was proven to be the optimum catalyst, among a series of activated ketones, for the organocatalytic oxidation of silanes to silanols 7a. Following our initial contribution, the same catalyst was found to promote both the oxidation of azines and tertiary amines to N ‐oxides7b and olefins to epoxides 7c.…”

Section: Resultsmentioning

confidence: 88%