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Synthesis 2018; 50(13): 2587-2594
DOI: 10.1055/s-0036-1591577
DOI: 10.1055/s-0036-1591577
paper
A Rapid Method to Aromatic Aminoalkyl Esters via the Catalyst-Free Difunctionalization of C–N Bonds
This research was supported by the National Natural Science Foundation of China (21463027) and Jiangxi Provincial Department of Education (KJLD14090).Further Information
Publication History
Received: 27 February 2018
Accepted after revision: 02 April 2018
Publication Date:
12 June 2018 (online)
Abstract
A novel multicomponent reaction involving a direct C–N esterification/arylation has been developed. This catalyst-free process was conducted with cyclic tertiary amines via a facile C–N cleavage to provide the alkyl group and nitrogen source. The operationally simple method to rapidly combine cyclic tertiary amines, haloazaarenes and carboxylic acids (or anhydrides) affords an efficient access to aromatic aminoalkyl esters, potential drug-like products, in good to excellent yields.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1591577. Included are copies of 1H and 13C NMR spectra for all compounds.
- Supporting Information
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Reviews on C–H bond activation:
Reviews on C–C bond activation:
Reviews on C–N bond activation:
Selected examples of the esterification of C–H bonds:
Selected examples of the esterification of C–C bonds:
Selected examples of the transition-metal-free esterification of C–H bonds: