Oxidative cycloaddition of hydroxamic acids with dienes or guaiacols mediated by iodine(III) reagents

Hisato Shimizu, Akira Yoshimura, Keiichi Noguchi, Victor N. Nemykin, Viktor V. Zhdankin, Akio Saito

Research output: Contribution to journalArticlepeer-review

2 Scopus citations

Abstract

[Bis(trifluoroacetoxy)iodo]benzene (BTI) and (diacetoxyiodo)benzene (DIB) efficiently promote the formation of acylnitroso species from hydroxamic acids in the presence of various dienes to give the corresponding hetero-Diels-Alder (HDA) adducts in moderate to high yields. The present method could be applied to the HDA reactions of acylnitroso species with o-benzoquinones generated by the oxidative dearomatization of guaiacols.

Original languageEnglish (US)
Pages (from-to)531-536
Number of pages6
JournalBeilstein Journal of Organic Chemistry
Volume14
DOIs
StatePublished - Feb 28 2018

Bibliographical note

Publisher Copyright:
© 2018 Shimizu et al.

Keywords

  • Acylnitroso
  • Benzoquinone
  • Cycloaddition
  • Dearomatization
  • Iodine(III)

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