A tandem 1,3-sulfur migration followed
by iodocyclization reaction of propargylic sulfides
in the presence of NIS in HFIP has been developed
to synthesize indene-based β-iodoalkenyl sulfides.
The choice of the reaction media is crucial to
promote the reaction. The proposed mechanism
involving the initial NIS activation by HFIP and
favoring the sulfur migration of the starting propargylic thioether via cationic intermediates is experimentally supported. In addition, the suitability of
selected indene-based β-iodoalkenyl sulfides as
building blocks for subsequent C C bond-forming
reactions has been demonstrated.
