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Relevant academic research and scientific papers

Singlet oxygen photo-oxygenation in water/pluronic F-127 hydrogels: Increased reaction efficiency coupled with a switch in regioselectivity

Pluronic F-127 hydrogels are highly efficient microenvironments for photochemical reactions, as demonstrated for singlet oxygen reactions of monoalkenes. Nonpolar substrates are localized in the nanosized polymer compartment, which can be visualized by neutron scattering. The efficiency of 1O2 reactions is strongly increased for tiglate derivatives and the regioselectivity of the ene reaction of trisubstituted alkenes is completely switched in comparison with solution phase and inverted in comparison with intrazeolite photo-oxygenations.

Stereoselectivity in ene reactions with 1O2: Matrix effects in polymer supports, photo-oxygenation of organic salts and asymmetric synthesis

The ene reaction of chiral allylic alcohols is applied as a tool for the investigation of intrapolymer effects by means of the stereoselectivity of the singlet-oxygen addition. The diastereo selectivity strongly depends on the structure of the polymer, th

Selective C-H Allylic Oxygenation of Cycloalkenes and Terpenoids Photosensitized by [Cu(Xantphos)(neoc)]BF4

We present herein for the first time the use of the [Cu(Xantphos)(neoc)]BF4 as a photocatalyst for the selective C-H allylic oxygenation of cycloalkenes into the corresponding allylic hydroperoxides or alcohols in the presence of molecular oxygen. The proposed methodology affords the products at good yields and has also been applied successfully to several bioactive terpenoids, such as geraniol, linalool, β-citronellol, and phytol. A mechanistic study involving also kinetic isotope effects (KIEs) supports the proposed singlet oxygen-mediated reaction. On the basis of the high chemoselectivity and yields and the fast and clean reaction processes observed, the present catalytic system, [Cu(Xantphos)(neoc)]BF4, has also been applied to the synthesis, at a laboratory scale, of the cis-Rose oxide, a well-known perfumery ingredient used in rose and geranium perfumes.

A method to determine the correct photocatalyst concentration for photooxidation reactions conducted in continuous flow reactors

When conducting a photooxidation reaction, the key question is what is the best amount of photocatalyst to be used in the reaction? This work demonstrates a fast and simple method to calculate a reliable concentration of the photocatalyst that will ensure an efficient reaction. The determination is based on shifting the calculation away from the concentration of the compound to be oxidized to utilizing the limitations on the total light dose that can be delivered to the catalyst. These limitations are defined by the photoflow setup, specifically the channel height and the emission peak of the light source. This method was tested and shown to work well for three catalysts with different absorption properties through using LEDs with emission maxima close to the absorption maximum of each catalyst.

An entirely solvent-free photooxygenation of olefins under continuous flow conditions

Photooxygenations of alkenes with singlet oxygen are a versatile, atom-economical transformation. The choice of solvents is key to the success of this oxyfunctionalization with direct impact on the solubility of substrates, the lifetime of the reactive oxygen species, and the up-scaling of the process. We report an entirely solvent-free continuous-flow photooxygenation that operates at very high substrate/sensitizer ratios and enables high space-time yields.

“Dark” Singlet Oxygen Made Easy

An operationally simple continuous flow generator of “dark” singlet oxygen has been developed. The singlet oxygen was efficiently reacted with several chemical traps to give the corresponding oxygenated products in high yields. The developed “dark” singlet oxygen generator has been successfully applied in the synthesis of the antimalarial drug artemisinin.

Continuous flow photooxygenation of monoterpenes

Photooxygenation of monoterpenes was conducted in two continuous flow reactors. The first, suitable for lab-scale research, had a maximum yield of 99.9%, and the second, focused on industrial applications, showed a daily output that was 270.0-fold higher than that in batch systems. The use of sunlight instead of an LED lamp gave 68.28% conversion.

Synergy between bis(dimethyldioctylammonium) molybdate and tetraethylene glycol monooctyl ether: A winning combination for interfacial catalysis in thermo-controlled and switchable microemulsions

A simple thermo-responsive one-phase microemulsion (μem) is designed to enable the dark singlet oxidation of organic substrates while allowing a straightforward separation of the catalytic surfactant and products in two distinct phases by cooling down the reaction medium. This latter is prepared by combining a small amount (1%) of the catalytic surfactant bis(dimethyldioctylammonium) molybdate, [DiC8]2[MoO4], with the nonionic amphiphile tetraethylene glycol monooctyl ether, C8E4. Tensiometry and dynamic light scattering are used to rationalize the synergy between the two surfactants which strongly interact. The oxidation takes place in the effective one-phase Winsor IV system which separates into two phases (μem + oil, i.e. Winsor I) just by temperature change thanks to the presence of the thermosensitive C8E4. The thermal-controlled nanostructured reaction medium is applied to the ene reaction, [4+2] cycloaddition and sulfide oxidation.

SEPARATION TECHNIQUE, PHOTO-OXIDATION OF ORGANIC SUBSTRATES, AND PHOTO CATALYSTS

A method for photo-oxidising an organic substrate to form an organic product is disclosed comprising: a) mixing oxygen, a supercritical fluid, a photocatalyst, a liquid fluorous solvent and an organic substrate to form a mixture; and b) irradiating the mixture to form an organic product. Also disclosed is a method for separating a photocatalyst from an organic product comprising the steps of: a) providing a mixture comprising a supercritical fluid; an organic product; a fluorous solvent; a photocatalyst; and optionally an organic substrate and optionally oxygen; wherein the organic product, fluorous solvent, photocatalyst and optional organic substrate and optional oxygen are dissolved in the supercritical fluid; and b) reducing the pressure of the mixture to a pressure below the critical pressure of the supercritical fluid in order to form a gaseous phase.

SEPARATION TECHNIQUE, PHOTO-OXIDATION OF ORGANIC SUBSTRATES, AND PHOTO CATALYSTS

A method for photo -oxidising an organic substrate to form an organic product is disclosed comprising: a) mixing oxygen, a supercritical fluid, a photocatalyst, a liquid fluorous solvent and an organic substrate to form a mixture; and b) irradiating the mixture to form an organic product. Also disclosed is a method for separating a photocatalyst from an organic product comprising the steps of: a) providing a mixture comprising a supercritical fluid; an organic product; a fluorous solvent; a photocatalyst; and optionally an organic substrate and optionally oxygen; wherein the organic product, fluorous solvent, photocatalyst and optional organic substrate and optional oxygen are dissolved in the supercritical fluid; and b) reducing the pressure of the mixture to a pressure below the critical pressure of the supercritical fluid in order to form a gaseous phase.