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Relevant academic research and scientific papers

Biocatalytic green alternative to existing hazardous reaction media: Synthesis of chalcone and flavone derivatives via the Claisen-Schmidt reaction at room temperature

Owing to the increasing amount of waste materials around the globe, the conversion of waste or secondary by-products to value-added products for various applications has gained significant interest. Herein, two novel agro-food waste products, Musa sp. 'Malbhog' peel ash (MMPA) and Musa Champa Hort. ex Hook. F. peel ash (MCPA) are used as catalysts to promote an inexpensive, efficient and eco-friendly carbon-carbon bond forming crossed aldol reaction at room temperature in solvent free conditions. Furthermore, the resulting products were subjected to reactions with these promoters in an oxygen atmosphere and led to the formation of novel flavone derivatives. Moreover, the used catalysts were properly characterized using different sophisticated analytical techniques such as Fourier-transform infrared spectroscopy (FT-IR), X-ray diffractometry (XRD), Brunauer-Emmett-Teller analysis (BET), Raman spectroscopy, scanning electron microscopy energy dispersive X-ray spectroscopy (SEM-EDS), transition electron microscopy (TEM), X-ray photoelectron spectroscopy (XPS) and thermogravimetric analysis (TGA) along with element detection using atomic absorption spectroscopy and ion chromatographic methods. These two approaches are metal free, as well as being devoid of any extra additives, co-catalysts, harsh conditions, the use of column chromatography for purification and result in a higher yield of the product within a short space of time. The catalytic abilities of the promoter were also examined to synthesize important bioactive molecules such as butein and apigenin at room temperature. With gram scale synthesis of the chalcone derivatives, the used catalysts (MMPA and MCPA) were further reused for five cycles and did not demonstrate any loss in catalytic activity.

Enantioselective Diels-Alder Reactions of Cyclohexa-1,3-diene and Chalcones Catalyzed by Intramolecular Silicon-Sulfur Lewis Pairs as Chiral Lewis Acids

The stereoselective preparation of diastereomeric dihydrosilepine-derived silicon cations decorated with another binaphthyl unit at the silicon atom is described. A sulfide donor attached to that additional binaphthyl substituent forms an intramolecular Lewis pair with the electron-deficient silicon atom, as verified by 29Si NMR spectroscopy. Both chiral sulfur-stabilized silicon cations act as catalysts in the difficult Diels-Alder reaction of cyclohexa-1,3-diene and chalcone derivatives. Both Lewis acids induce enantioselectivity, but the S,S relative configuration is superior to the S,R configuration. With the former diastereomer, enantiomeric excesses of close to 60% are obtained. These values are the highest achieved to date in this seemingly trivial cycloaddition.

Strategic Application and Transformation of ortho-Disubstituted Phenyl and Cyclopropyl Ketones to Expand the Scope of Hydrogen Borrowing Catalysis

The application of an iridium-catalyzed hydrogen borrowing process to enable the formation of α-branched ketones with higher alcohols is described. In order to facilitate this reaction, ortho-disubstituted phenyl and cyclopropyl ketones were recognized as crucial structural motifs for C-C bond formation. Having optimized the key catalysis step, the ortho-disubstituted phenyl products could be further manipulated by a retro-Friedel-Crafts acylation reaction to produce synthetically useful carboxylic acid derivatives. In contrast, the cyclopropyl ketones underwent homoconjugate addition with several nucleophiles to provide further functionalized branched ketone products.

Iridium(I)-catalyzed regioselective C-H activation and hydrogen-isotope exchange of non-aromatic unsaturated functionality

Isotopic labelling is a key technology of increasing importance for the investigation of new C-H activation and functionalization techniques, as well as in the construction of labelled molecules for use within both organic synthesis and drug discovery. Herein, we report for the first time selective iridium-catalyzed C-H activation and hydrogen-isotope exchange at the β-position of unsaturated organic compounds. The use of our highly active [Ir(cod)(IMes)(PPh3)][PF6] (cod = 1, 5-cyclooctadiene) catalyst, under mild reaction conditions, allows the regioselective β-activation and labelling of a range of α, β-unsaturated compounds with differing steric and electronic properties. This new process delivers high levels of isotope incorporation over short reaction times by using low levels of catalyst loading.

2'-Substituted chalcone derivatives as inhibitors of interleukin-1 biosynthesis

A series of 2'-substituted chalcone derivatives has been found to show potent inhibition of the production of IL-1β from human peripheral blood monocytes stimulated with lipopolysaccharide (LPS), with IC50 values in the 0.2-5.0-μM range. Some members of the series have also shown inhibition of septic shock induced in mice by injection of LPS, although with low potency. Qualitative structure-activity relationships have shown that the enone is required for activity, which may be mediated by conjugate addition of a biological nucleophile to the chalcone. Electron-poor aromatic rings β to the ketone give enhanced potency. Although electronic effects in the other ring (directly attached to the ketone) are minimal, this ring must possess an ortho substituent for good activity without cytotoxicity, suggesting a degree of selectivity which would not be expected for simple, nonspecific alkylating agents.