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 Scopus citations

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 (US)
Pages (from-to)1016-1020
Number of pages5
JournalBeilstein Journal of Organic Chemistry
Volume14
DOIs
StatePublished - May 8 2018

Bibliographical note

Funding Information:
This work was supported by a research grant from the Russian Science Foundation (RSF-16-13-10081). A.S. is also thankful to JSPS Grant-in-Aid for Scientific Research (C, Grant No 15K07852) and to the JSPS Fund for the Promotion of Joint International Research (Grant No 16KK0199). V.V.Z. is thankful for support from the Office of the Vice President for Research, University of Minnesota.

Publisher Copyright:
© 2018 Yoshimura et al.;

Keywords

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

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