A smooth and practicable azido-iodination reaction of alkenes based on IPy2BF4 and Me3SiN3

Citation
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
Citations number
23
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ADVANCED SYNTHESIS & CATALYSIS
ISSN journal
16154150 → ACNP
Volume
343
Issue
4
Year of publication
2001
Pages
335 - 337
Database
ISI
SICI code
1615-4150(200105)343:4<335:ASAPAR>2.0.ZU;2-D
Abstract
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.