J. Barluenga et al., A smooth and practicable azido-iodination reaction of alkenes based on IPy2BF4 and Me3SiN3, ADV SYNTH C, 343(4), 2001, pp. 335-337
The reaction of alkenes with IPy2BF4 and Me3SiN3 under the influence of BF3
.OEt2 provides a mild an efficient entry to vicinal azidoiodoalkanes. Besid
es the simplicity of the experimental protocol and the convenience found in
the handling of the reagents, the use of stoichiometric amounts of the azi
de source is remarkable, and overrides the known and always troublesome dep
endence on large excesses of azide to accomplish this synthetically valuabl
e transformation.