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

Autor*innen

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

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

Volltext

Referenzen

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