Preparation, structure, and reactivity of bicyclic benziodazole: A new hypervalent iodine heterocycle

Akira Yoshimura, Michael T. Shea, Cody L. Makitalo, Melissa E. Jarvi, Gregory T. Rohde, Akio Saito, Mekhman S. Yusubov, Viktor V. Zhdankin

Research output: Contribution to journalArticlepeer-review

4 Citations (Scopus)

Abstract

A new bicyclic organohypervalent iodine heterocycle derivative of benziodazole was prepared by oxidation of 2-iodo-N,N'-diiso-propylisophthalamide with m-chloroperoxybenzoic acid under mild conditions. Single crystal X-ray crystallography of this compound revealed a five-membered bis-heterocyclic structure with two covalent bonds between the iodine atom and the nitrogen atoms. This novel benziodazole is a very stable compound with good solubility in common organic solvents. This compound can be used as an efficient reagent for oxidatively assisted coupling of carboxylic acids with alcohols or amines to afford the corresponding esters or amides in moderate yields.

Original languageEnglish
Pages (from-to)1016-1020
Number of pages5
JournalBeilstein Journal of Organic Chemistry
Volume14
DOIs
Publication statusPublished - 8 May 2018

Keywords

  • Benziodazole
  • Biheterocycles
  • Hypervalent iodine
  • Iodine
  • Oxidatively assisted esterification

ASJC Scopus subject areas

  • Organic Chemistry

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