Transition-metal-free Csp3–Csp doubly decarboxylative coupling of amino acids and propiolic acids

A3-coupling and decarboxylative A3-coupling is an important protocol for constructing propargylamines. However, the development of metal-free (decarboxylative) A3-coupling is still challenging. Herein, we describe a doubly decarboxylative coupling of amino acids, propiolic acids, and aldehydes under...

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Veröffentlicht in:Sustainable chemistry and pharmacy 2024-04, Vol.38, Article 101441
Hauptverfasser: Hu, Junduo, Liu, Leyan, Wang, Haixiang, Huang, Liliang, Gao, Huanmei, Feng, Huangdi
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Sprache:eng
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Zusammenfassung:A3-coupling and decarboxylative A3-coupling is an important protocol for constructing propargylamines. However, the development of metal-free (decarboxylative) A3-coupling is still challenging. Herein, we describe a doubly decarboxylative coupling of amino acids, propiolic acids, and aldehydes under metal-free conditions. It is worth noting that choosing the kind of aldehydes is crucial for controlling the chemoselectivity of the reaction. The use of glyoxylate ester furnished ester-containing propargylamines in good yield via a cascade process of decarboxylation and decarboxylative coupling. Both aliphatic and aromatic aldehydes were transformed into the decarboxylative A3-coupling products. [Display omitted] •Potential applications of propargylamines in the fields of medicinal and organic chemistry.•The sustainable synthesis of propargylamines was studied under catalyst-free conditions.•A doubly decarboxylative approach was employed to optimize the propargylamine formation.•Readily available feedstocks and broad substrate scope.
ISSN:2352-5541
2352-5541
DOI:10.1016/j.scp.2024.101441