Reductive approach to nitrones from N-Siloxyamides and N-Hydroxyamides

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

Research output: Contribution to journalArticle

16 Citations (Scopus)

Abstract

This article describes the full details of our reductive approach to nitrones from amides. Reduction of N-siloxyamides with the Schwartz reagent [Cp2ZrHCl], followed by addition of an acid provided functionalized nitrones. The developed conditions were then extended to a catalytic version with the Vaska complex [IrCl(CO)(PPh3)2] and (Me2HSi)2O starting from N-hydroxyamides. 1HNMR studies of the Ir-catalyzed reaction revealed that the developed conditions promoted two different types of catalytic reactions including dehydrosilylation of an N-hydroxyl group and subsequent hydrosilylation of an amide carbonyl. A salient feature of our methods is their high chemoselectivity in the presence of a variety of functional groups. In addition, our reductive methods enabled concise synthesis of cyclic and macrocyclic nitrones, which are known to be challenging compounds to access by conventional methods.

Original languageEnglish
Pages (from-to)893-904
Number of pages12
JournalBulletin of the Chemical Society of Japan
Volume90
Issue number8
DOIs
Publication statusPublished - 2017

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Amides
Hydrosilylation
Carbon Monoxide
Hydroxyl Radical
Functional groups
Acids
nitrones
Schwartz reagent

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Reductive approach to nitrones from N-Siloxyamides and N-Hydroxyamides. / Katahara, Seiya; Kobayashi, Shoichiro; Fujita, Kanami; Matsumoto, Tsutomu; Satou, Takaaki; Chida, Noritaka.

In: Bulletin of the Chemical Society of Japan, Vol. 90, No. 8, 2017, p. 893-904.

Research output: Contribution to journalArticle

Katahara, Seiya ; Kobayashi, Shoichiro ; Fujita, Kanami ; Matsumoto, Tsutomu ; Satou, Takaaki ; Chida, Noritaka. / Reductive approach to nitrones from N-Siloxyamides and N-Hydroxyamides. In: Bulletin of the Chemical Society of Japan. 2017 ; Vol. 90, No. 8. pp. 893-904.
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