Search

A series of (un-)charged NHC derivatives bearing two pentadecyl chains in the backbone was studied in detail to find cooperative effects between the membrane and the NHC derivative. The tendency to show lipid-like behavior is dependent on the properties of the NHC derivative headgroup, which can be modified on demand. The surface activity was investigated by film balance measurements, epifluorescence microscopy, and differential scanning calorimetry. Additionally the cytotoxicity was evaluated against different cell lines such as eukaryotic tumor cell lines. These novel lipid-like NHC derivatives offer a broad spectrum for biological applications., (© 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.)

A detailed account of the synthesis of chiral bicyclic guanidinium salts is presented. This work represents the first systematic investigation of an approach toward the challenging target molecules via a key guanylation step employing di(imidazole-1-yl)methanimine (6) followed by a two-fold cyclization, which resulted in guanidinium salts 8 and 10. Factors governing the regioselectivity of the final cyclization step are discussed based on further data obtained in the course of the attempted syntheses of two additional bicyclic guanidinium salts.

Herein, we report a new visible-light-promoted strategy to access radical trifluoromethylthiolation reactions by combining halide and photoredox catalysis. This approach allows for the synthesis of vinyl-SCF3 compounds of relevance in pharmaceutical chemistry directly from alkenes under mild conditions with irradiation from household light sources. Furthermore, alkyl-SCF3-containing cyclic ketone and oxindole derivatives can be accessed by radical-polar crossover semi-pinacol and cyclization processes. Inexpensive halide salts play a crucial role in activating the trifluoromethylthiolating reagent towards photoredox catalysis and aid the formation of the SCF3 radical., (© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.)

A general and efficient methodology for the direct transition metal free trifluoromethylthiolation of a broad range of biologically relevant N-heteroarenes is reported employing abundant sodium chloride as the catalyst. This method is operationally simple, exhibits high functional group tolerance, and does not require protecting groups., (© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.)

A highly selective arylation of a number of polyaromatic hydrocarbons (PAHs) with aryliodonium salts and Pd/C as the only reagent is reported. The first C-H functionalization of triphenylene is explored, and proceeds at the most sterically hindered position. This non-chelate assisted C-H functionalization extends the reactivity profile of Pd/C and provides controlled access to π-extended PAHs, an important aspect of work towards the preparation of nanographenes. Mechanistic studies suggest in situ formation of catalytically active insoluble nanoparticles, and that the reaction likely proceeds via a Pd(0)/Pd(ii) type reaction manifold.