Metal-Free Transamidation of Primary Amides using Trimethylsilyl Chloride

Subeen Yu; Kwang Ho Song; Sunwoo Lee

doi:10.1002/ajoc.201900216

Metal-Free Transamidation of Primary Amides using Trimethylsilyl Chloride

Subeen Yu, Kwang Ho Song, Sunwoo Lee

Department of Chemical and Biological Engineering

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

11 Citations (Scopus)

Abstract

A metal-free transamidation of primary amides was developed. Trimethylsilyl chloride (TMSCl) acted as the activator in transamidation. In the presence of TMSCl, primary amides reacted with primary amines to yield transamidated secondary amides in NMP solvent. The transamidation of benzamide with secondary amines for the formation of tertiary amides succeeds in an NMP/CHCl₃ solvent mixture.

Original language	English
Pages (from-to)	1613-1616
Number of pages	4
Journal	Asian Journal of Organic Chemistry
Volume	8
Issue number	9
DOIs	https://doi.org/10.1002/ajoc.201900216
Publication status	Published - 2019 Sep 1

Keywords

amides
amines
metal-free chemistry
transamidation
trimethylsilyl chloride

ASJC Scopus subject areas

Organic Chemistry

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10.1002/ajoc.201900216

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abstract = "A metal-free transamidation of primary amides was developed. Trimethylsilyl chloride (TMSCl) acted as the activator in transamidation. In the presence of TMSCl, primary amides reacted with primary amines to yield transamidated secondary amides in NMP solvent. The transamidation of benzamide with secondary amines for the formation of tertiary amides succeeds in an NMP/CHCl3 solvent mixture.",

keywords = "amides, amines, metal-free chemistry, transamidation, trimethylsilyl chloride",

author = "Subeen Yu and {Ho Song}, Kwang and Sunwoo Lee",

note = "Funding Information: This research was supported by the National Research Foundation of Korea (NRF) grant funded by the Korea government (NRF-2012 M3 A7B4049655, NRF-2015R1 A4 A1041036). The spectral data were obtained from the Gwangju center and HRMS data from the Daegu center of Korea Basic Science Institute. Publisher Copyright: {\textcopyright} 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim",

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doi = "10.1002/ajoc.201900216",

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T1 - Metal-Free Transamidation of Primary Amides using Trimethylsilyl Chloride

AU - Yu, Subeen

AU - Ho Song, Kwang

AU - Lee, Sunwoo

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PY - 2019/9/1

Y1 - 2019/9/1

N2 - A metal-free transamidation of primary amides was developed. Trimethylsilyl chloride (TMSCl) acted as the activator in transamidation. In the presence of TMSCl, primary amides reacted with primary amines to yield transamidated secondary amides in NMP solvent. The transamidation of benzamide with secondary amines for the formation of tertiary amides succeeds in an NMP/CHCl3 solvent mixture.

AB - A metal-free transamidation of primary amides was developed. Trimethylsilyl chloride (TMSCl) acted as the activator in transamidation. In the presence of TMSCl, primary amides reacted with primary amines to yield transamidated secondary amides in NMP solvent. The transamidation of benzamide with secondary amines for the formation of tertiary amides succeeds in an NMP/CHCl3 solvent mixture.

KW - amides

KW - amines

KW - metal-free chemistry

KW - transamidation

KW - trimethylsilyl chloride

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DO - 10.1002/ajoc.201900216

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EP - 1616

JO - Asian Journal of Organic Chemistry

JF - Asian Journal of Organic Chemistry

SN - 2193-5807

IS - 9

ER -

Metal-Free Transamidation of Primary Amides using Trimethylsilyl Chloride

Abstract

Keywords

ASJC Scopus subject areas

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