A Practical Approach for the Transamidation of N,N-Dimethyl Amides with Primary Amines Promoted by Sodium tert-Butoxide under Solvent-Free Conditions

Rui Zhang; Jun-Chao Zhang; Wei-Yi Zhang; Yu-Qing He; Hua Cheng; Cheng Chen; Yu-Cheng Gu

doi:10.1055/s-0040-1705892

Synthesis, Inhaltsverzeichnis

Synthesis 2020; 52(21): 3286-3294
DOI: 10.1055/s-0040-1705892

special topic

Recent Advances in Amide Bond Formation

A Practical Approach for the Transamidation of N,N-Dimethyl Amides with Primary Amines Promoted by Sodium tert-Butoxide under Solvent-Free Conditions

Rui Zhang

^aDepartment of Chemical Engineering and Food Science, Hubei University of Arts and Science, Xiangyang 441053, P. R. of China eMail: cch510@126.com

,

Jun-Chao Zhang

^aDepartment of Chemical Engineering and Food Science, Hubei University of Arts and Science, Xiangyang 441053, P. R. of China eMail: cch510@126.com

,

Wei-Yi Zhang

^aDepartment of Chemical Engineering and Food Science, Hubei University of Arts and Science, Xiangyang 441053, P. R. of China eMail: cch510@126.com

,

Yu-Qing He

^aDepartment of Chemical Engineering and Food Science, Hubei University of Arts and Science, Xiangyang 441053, P. R. of China eMail: cch510@126.com

,

Hua Cheng∗

^aDepartment of Chemical Engineering and Food Science, Hubei University of Arts and Science, Xiangyang 441053, P. R. of China eMail: cch510@126.com

,

Cheng Chen ∗

^bState Key Laboratory of Advanced Technology for Materials Synthesis and Processing, Wuhan University of Technology, 122 Luoshi Road, Wuhan 430070, P. R. of China eMail: chengchen@whut.edu.cn

,

Yu-Cheng Gu

^cSyngenta, Jealott’s Hill International Research Centre, Bracknell, Berkshire, RG42 6EY, UK

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Abstract

Alle Artikel dieser Rubrik

This paper is dedicated to Professor Youyou Tu, the 2015 Nobel Prize Laureate of Physiology or Medicine, on the occasion of her 90^th birthday

Abstract

A practical sodium tert-butoxide (NaOtBu)-mediated protocol is disclosed for the transamidation of various N,N-dimethyl amides with primary amines to afford the corresponding amides in moderate to good yields at room temperature under solvent-free conditions. This protocol features a facile work-up procedure and good functional group compatibility, especially for N,N-dimethyl amides with long-chain alkyl groups and heteroatom-containing amines. Notably, a few representative gram-scale reactions proceed smoothly to furnish the desired amides in high yields, which demonstrates the potential of this process for further practical applications. Several control experiments are carried out and a plausible mechanism is provided.

Key words

NaOtBu - transamidation - N,N-dimethyl amides - primary amines - solvent-free - gram-scale

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Referenzen

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