A general and atom-efficient continuous-flow approach to prepare amines, amides and imines via reactive -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 -chloramines directly, avoiding purification and isolation steps. 2-Chloramines were produced from the reaction of styrenes with -alkyl--sulfonyl--chloramines, whilst -alkyl or -dialkyl--chloramines reacted with anisaldehyde in the presence of -BuOH oxidant to afford amides. Primary and secondary imines were produced under continuous conditions from the reaction of -chloramines with base, with one example subsequently reduced under asymmetric conditions to produce a chiral amine in 94% ee.