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Synthesis 2020; 52(21): 3286-3294
DOI: 10.1055/s-0040-1705892
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
This research was supported by the National Natural Science Foundation of China (Grant No. 21502062), the Scientific Research Program Guiding Project of Hubei Provincial Department of Education (Grant No. B2019135), the Teachers’ Scientific Research Ability Cultivation Fund, Hubei University of Arts and Science (Natural Science, Grant No. 2018kypy001), the Foundation of Hubei University of Arts and Science (Grant No. 2059057), the Open Foundation of Discipline of Hubei University of Arts and Science (Grant Nos. XK2019038, XK2019039), and the National Natural Science Foundation Cultivation Project of Hubei University of Arts and Science (Grant No. 2019kypygp003).
This paper is dedicated to Professor Youyou Tu, the 2015 Nobel Prize Laureate of Physiology or Medicine, on the occasion of her 90th 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-scaleSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1705892.
- Supporting Information
Publication History
Received: 29 May 2020
Accepted after revision: 22 July 2020
Article published online:
08 September 2020
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