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

Haoyi Yao; Yun Tang; Kana Yamamoto

doi:10.1016/j.tetlet.2012.07.024

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

Haoyi Yao, Yun Tang, Kana Yamamoto^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

38 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 language	English
Pages (from-to)	5094-5098
Number of pages	5
Journal	Tetrahedron Letters
Volume	53
Issue number	38
DOIs	https://doi.org/10.1016/j.tetlet.2012.07.024
Publication status	Published - 2012 Sept 19
Externally published	Yes

Keywords

Amide
Electron spin resonance
Hypervalent iodine
N-Hydroxysuccinimide
Oxidation

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2012.07.024

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title = "Metal-free oxidative amide formation with N-hydroxysuccinimide and hypervalent iodine reagents",

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.",

keywords = "Amide, Electron spin resonance, Hypervalent iodine, N-Hydroxysuccinimide, Oxidation",

author = "Haoyi Yao and Yun Tang and Kana Yamamoto",

note = "Funding Information: This work was supported by funding from the University of Toledo (K.Y., New Faculty Start Up Fund; University of Toledo Summer Research Award, 2010). We thank Dr. Yong-Wah Kim for assistance with ESR analyses. We also thank Dr. Chao Hang of Bristol-Myers Squibb for helpful discussions on isotope effect experiments. ",

year = "2012",

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day = "19",

doi = "10.1016/j.tetlet.2012.07.024",

language = "English",

volume = "53",

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journal = "Tetrahedron Letters",

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TY - JOUR

T1 - Metal-free oxidative amide formation with N-hydroxysuccinimide and hypervalent iodine reagents

AU - Yao, Haoyi

AU - Tang, Yun

AU - Yamamoto, Kana

N1 - Funding Information: This work was supported by funding from the University of Toledo (K.Y., New Faculty Start Up Fund; University of Toledo Summer Research Award, 2010). We thank Dr. Yong-Wah Kim for assistance with ESR analyses. We also thank Dr. Chao Hang of Bristol-Myers Squibb for helpful discussions on isotope effect experiments.

PY - 2012/9/19

Y1 - 2012/9/19

N2 - 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.

AB - 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.

KW - Amide

KW - Electron spin resonance

KW - Hypervalent iodine

KW - N-Hydroxysuccinimide

KW - Oxidation

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DO - 10.1016/j.tetlet.2012.07.024

M3 - Article

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SN - 0040-4039

VL - 53

SP - 5094

EP - 5098

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 38

ER -

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

Abstract

Keywords

ASJC Scopus subject areas

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