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 |
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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.
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•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. |
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ISSN: | 2352-5541 2352-5541 |
DOI: | 10.1016/j.scp.2024.101441 |