Synthesis, structure, and chemoselective reactivity of N-(2-iodylphenyl) acylamides: Hypervalent iodine reagents bearing a pseudo-six-membered ring.scaffold

Uladzimir Ladziata, Alexey Y. Koposov, Ka Y. Lo, Jeff Willging, Victor N. Nemykin, Viktor Zhdankin

Research output: Contribution to journalArticlepeer-review

46 Scopus citations

Abstract

A pseudo-benziodoxazine structure with intramolecular secondary I⋯O bonding, as shown by X-ray analysis, is seen in a series of N-(2-iodylphenyl) acylamides prepared from 2-iodoaniline (see scheme). These compounds contain a six-membered pseudocyclic scaffold about an iodine(v) center and are able to oxidize either alcohols or sulfides, with the reactivity depending largely on the substitution pattern on the amide group adjacent to the iodyl moiety. (Chemical Equation Presented).

Original languageEnglish (US)
Pages (from-to)7127-7131
Number of pages5
JournalAngewandte Chemie - International Edition
Volume44
Issue number43
DOIs
StatePublished - Nov 3 2005

Keywords

  • Alcohols
  • Hypervalent iodine
  • Oxidation
  • Regioselectivity
  • Thiols

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