Linbei Deng

Background and Originality Content The amide bond is the backbone for peptides and a vast number of natural products, bioactive molecules, and marketed pharmaceuticals (Figure 1a, for example, flecainide, bezafibrate, flutamide, moclobemide, and lidocaine).[1-4] Approximately a quarter of current marketed drugs and drug lead molecules contain amide linkages,[5, 6] or carbamates that are also present in many pharmaceutical compounds (for example, rivastigmine).

Abstract N-monofluoromethyl (N-CH2F) amides, combining amide and monofluoromethyl motifs, represent a practical modification of the amide bond that can mimic N-CH3 amides. Despite the potential value in transforming peptides and peptidomimetics with N-CH2F, the very existence of this structure has been controversial. Here we report the preparation of N-CH2F amides and carbamates via simple and robust chemical methods.