Hydrogen isotopically labelledc ompoundsa re essential diagnostic tools in drug research and development, as they provide vital informationa bout the biological metabolism of drug candidates and their metabolites. Herein we report ap hotoredox-initiated hydrogen atom transfer(HAT) protocol which efficiently and selectively introduces deuterium or tritium at C(sp 3)ÀHb onds, utilizing heavy water (D 2 Oo rT 2 O) as the hydrogen isotope source, and ag uanidine base.T his protocol has been successfully appliedto the incorporationo fd euteriumi ns everal amino acids (lysine, glycine and proline) and small peptides. Finally,t he method has been applied to tritium,b ecause tritium-labelled peptides are essential for application in biological experiments,s uch as ligand-binding assays,o ra bsorption, distribution, metabolism, and excretion (ADME) studies.

The dehydrogenative C-N cross-coupling of unprotected, secondary anilines through ortho-N-carbazolation has been achieved using a Ru catalytic system with O2 as the terminal oxidant. The reactions proceed in an intermolecular fashion, selectively in the ortho position. Implications for the field of organic synthesis are discussed.

This personal account summarizes our contribution to the ion pairing organocatalysis mainly by use of chiral quaternary or tertiary ammonium fluorides, aryloxides and carboxylates. Starting from an experimental observation, we were able to develop several approaches for the enantioselective protonation of silyl enolates and enol esters giving rise to chiral carbonyl compounds bearing a stereogenic center at the α-position. Moving from protonation to deprotonation reactions, chiral ammonium ion pair catalysts were successfully applied to several asymmetric transformations such as an Henry reaction or a direct vinylogous aldol reaction to cite a few. An outlook of further possible developments in this field of research will also be discussed.

An original organocatalyzed enantioselective protonation sequence of a transient quaternary ammonium enolate species has been developed by starting from readily available disubstituted Meldrum's acid derivatives and phenols. Under phase‐transfer‐catalytic (PTC) conditions, chiral nonracemic 2‐aryl propionic ester derivatives were obtained in good isolated yields with enantioselectivities up to 70 % ee. The usefulness of the approach was demonstrated by the synthesis of enantioenriched (S)‐ibuprofen.