A general and atom-efficient continuous-flow approach to prepare amines, amides and imines via reactive N -chloramines.

Chloramines are an important class of reagents, providing a convenient source of chlorine or electrophilic nitrogen. However, the instability of these compounds is a problem which makes their isolation and handling difficult. To overcome these hazards, a continuous-flow approach is reported which generates and immediately reacts N -chloramines directly, avoiding purification and isolation steps. 2-Chloramines were produced from the reaction of styrenes with N -alkyl- N -sulfonyl- N -chloramines, whilst N -alkyl or N,N' -dialkyl- N -chloramines reacted with anisaldehyde in the presence of t -BuO ₂ H oxidant to afford amides. Primary and secondary imines were produced under continuous conditions from the reaction of N -chloramines with base, with one example subsequently reduced under asymmetric conditions to produce a chiral amine in 94% ee.