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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.

Use the head! A set of (un-)charged NHC derivatives bearing two pentadecyl-chains in the backbone was studied in detail. The lipid-like behavior depends on the properties of the headgroup of the NHC derivatives. The surface activity was investigated by film balance measurements, epifluorescence microscopy and differential scanning calorimetry. Additionally the cytotoxicity was evaluated against different cell lines. These novel lipid-like NHC derivatives offer a broad spectrum for biological applications.

An unprecedented and challenging radical–radical cross-coupling of α-aminoalkyl radicals with monofluoroalkenyl radicals derived from gem-difluoroalkenes was achieved. This first example of tandem C(sp³)−H and C(sp²)−F bond functionalization through visible-light photoredox catalysis offers a facile and flexible access to privileged tetrasubstituted monofluoroalkenes under very mild reaction conditions. The striking features of this redox-neutral method in terms of scope, functional-group tolerance, and regioselectivity are illustrated by the late-stage fluoroalkenylation of complex molecular architectures such as bioactive (+)-diltiazem, rosiglitazone, dihydroartemisinin, oleanic acid, and androsterone derivatives, which represent important new α-amino C−H monofluoroalkenylations.

Privileged products: A α-C(sp³)−H monofluoroalkenylation of unactivated tertiary amines through a mild, efficient, and redox-neutral route delivers privileged tetrasubstituted monofluoroalkenes under photoredox catalysis through the radical–radical cross- coupling of α-aminoalkyl radicals with monofluoroalkenyl radicals. This method enables the challenging late-stage monofluoroalkenylation of complex molecules.