1-Amido-3-(1H)-1,2-benziodoxoles: Stable amidoiodanes and reagents for direct amidation of organic substrates

✍ Scribed by Viktor V. Zhdankin; Marc McSherry; Brian Mismash; Jason T. Bolz; Jessica K. Woodward; Ruslan M. Arbit; Scott Erickson

• Book ID: 104255995
• Publisher: Elsevier Science
• Year: 1997
• Tongue: French
• Weight: 188 KB
• Volume: 38
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(96)02245-9

✦ Synopsis

Hypervalent iodine derivatives with I-N bonds are generally less common than those with I-O bonds. 1 Most of these compounds lack stability and are sensitive to moisture. The known compounds of this type are represented by iminoiodanes, PhI=NR, and azidoiodanes, ArI(N3)X.1 In particular, iminoiodanes have found some synthetic application as efficient reagents for direct aziridination of unsaturated organic substrates,1 while azidoiodanes are useful azidating reagents.l,2 Only few examples of the very unstable amidoiodanes, PhI[NHC(O)R]X (R = alkyl or aryl; X = OTs, OAc) are known. 3 In this communication we wish to report the preparation and chemical reactivity of stable amidoiodane s, derivatives of benziodoxole.

Amidobenziodoxoles 2 can be conveniently prepared in one step from the commercial 2-iodosylbenzoic acid 1, trimethylsilyltriflate and the appropriate amide, RNH 2 (R = acyl or tosyl). All five adducts 2a-e were isolated as thermally stable, white, non-hygroscopic, microcrystalline solids and identified by spectral data and elemental analyses. 4