Metal-free oxidative amide formation with N-hydroxysuccinimide and hypervalent iodine reagents

Haoyi Yao, Yun Tang, Kana Yamamoto

Research output: Contribution to journalArticle

30 Citations (Scopus)

Abstract

An oxidative amide formation using N-hydroxysuccinimide and hypervalent iodine reagents was developed. The method enables a wide range of aldehydes and amines to be coupled under mild reaction conditions providing amide in good to excellent yield. The radical species in the reaction mixture was observed for the first time using ESR measurement, and along with other mechanistic investigations, a plausible mechanism of the reaction was proposed.

Original languageEnglish
Pages (from-to)5094-5098
Number of pages5
JournalTetrahedron Letters
Volume53
Issue number38
DOIs
Publication statusPublished - 2012 Sep 19
Externally publishedYes

Fingerprint

Amides
Iodine
Metals
Aldehydes
Amines
Paramagnetic resonance
N-hydroxysuccinimide

Keywords

  • Amide
  • Electron spin resonance
  • Hypervalent iodine
  • N-Hydroxysuccinimide
  • Oxidation

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Metal-free oxidative amide formation with N-hydroxysuccinimide and hypervalent iodine reagents. / Yao, Haoyi; Tang, Yun; Yamamoto, Kana.

In: Tetrahedron Letters, Vol. 53, No. 38, 19.09.2012, p. 5094-5098.

Research output: Contribution to journalArticle

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