N-(2-iodylphenyl)acylamides - New pentavalent iodine oxidizing reagents

Uladzimir Ladziata, Viktor Zhdankin

Research output: Contribution to journalArticlepeer-review

81 Scopus citations

Abstract

This account describes design and synthetic utilization of new iodine(V) oxidizing reagents, N-(2-iodylphenyl)acylamides (NIPAs). NIPA reagents are soluble and stable pseudo-cyclic IBX analogues that are able to selectively oxidize either alcohols or sulfides, with the reactivity depending largely on the substitution pattern on the amido group adjacent to the iodyl moiety. A recyclable polymer-supported version of NIPA (NIPA resin) can conveniently be prepared in three simple steps. NIPA resin can effect smooth and efficient oxidation of a large variety of alcohols to the respective carbonyl compounds. Proline-based NIPA derivatives are promising chiral oxidants based on a pseudo-benziodoxazine scaffold.

Original languageEnglish (US)
Pages (from-to)527-537
Number of pages11
JournalSynlett
Issue number4
DOIs
StatePublished - Mar 1 2007

Keywords

  • Alcohols
  • Asymmetric synthesis
  • Iodine
  • Oxidations
  • Sulfides

Fingerprint Dive into the research topics of 'N-(2-iodylphenyl)acylamides - New pentavalent iodine oxidizing reagents'. Together they form a unique fingerprint.

Cite this