A modular synthesis of sulfondiimidoyl fluorides - the
double aza-analogues of sulfonyl fluorides - allowing variation of the
carbon and both nitrogen-substituents is reported. The chemistry uses
readily available organometallic reagents, commercial sulfinylamines,
simple electrophiles, and N-fluorobenzenesulfonimide (NFSI), as the
starting materials. The reactions are broad in scope, efficient, and
scalable. We show that the sulfondiimidoyl fluoride products can be
combined with amines to provide sulfondiimidamides, and with
organolithium reagents to provide sulfondiimines, and that reactivity
in these transformations can be modulated by variation of the
N-substituents.
