An Iridium-Catalyzed Reductive Approach to Nitrones from N-Hydroxyamides

Seiya Katahara, Shoichiro Kobayashi, Kanami Fujita, Tsutomu Matsumoto, Takaaki Satou, Noritaka Chida

Research output: Contribution to journalArticle

50 Citations (Scopus)

Abstract

An Ir-catalyzed reductive formation of functionalized nitrones from N-hydroxyamides was reported. The reaction took place through two types of iridium-catalyzed reactions including dehydrosilylation and hydrosilylation. The method showed high chemoselectivity in the presence of sensitive functional groups, such as methyl esters, and was successfully applied to the synthesis of cyclic and macrocyclic nitrones, which are known to be challenging compounds to access by conventional methods. 1H NMR studies strongly supported generation of an N-siloxyamide and an N,O-acetal as the actual intermediates.

Original languageEnglish
Pages (from-to)5246-5249
Number of pages4
JournalJournal of the American Chemical Society
Volume138
Issue number16
DOIs
Publication statusPublished - 2016 Apr 27

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Hydrosilylation
Iridium
Functional groups
Esters
Nuclear magnetic resonance
Acetals
nitrones
Proton Magnetic Resonance Spectroscopy

ASJC Scopus subject areas

  • Chemistry(all)
  • Catalysis
  • Biochemistry
  • Colloid and Surface Chemistry

Cite this

An Iridium-Catalyzed Reductive Approach to Nitrones from N-Hydroxyamides. / Katahara, Seiya; Kobayashi, Shoichiro; Fujita, Kanami; Matsumoto, Tsutomu; Satou, Takaaki; Chida, Noritaka.

In: Journal of the American Chemical Society, Vol. 138, No. 16, 27.04.2016, p. 5246-5249.

Research output: Contribution to journalArticle

Katahara, Seiya ; Kobayashi, Shoichiro ; Fujita, Kanami ; Matsumoto, Tsutomu ; Satou, Takaaki ; Chida, Noritaka. / An Iridium-Catalyzed Reductive Approach to Nitrones from N-Hydroxyamides. In: Journal of the American Chemical Society. 2016 ; Vol. 138, No. 16. pp. 5246-5249.
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