Harnessing ynamide activation to access deuterated carbonyls

Harnessing ynamide activation to access deuterated carbonyls

A simple and convenient synthesis of α-bisdeuterated imides is reported, hinging on the transient formation of keteniminium ions by treatment of ynamides with TfOD, followed by trapping with D2O. The products are obtained in good yields and with a high degree of deuterium incorporation. Gram-scale r...

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Veröffentlicht in:Tetrahedron 2021-06, Vol.90, p.132211, Article 132211
Hauptverfasser: Porte, Vincent, Zhang, Haoqi, Kaiser, Daniel, Maulide, Nuno
Format: Artikel
Sprache:eng
Schlagworte:
Deuteration
Imides
Isotope labeling
Keteniminium ions
Ynamide activation
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Zusammenfassung:A simple and convenient synthesis of α-bisdeuterated imides is reported, hinging on the transient formation of keteniminium ions by treatment of ynamides with TfOD, followed by trapping with D2O. The products are obtained in good yields and with a high degree of deuterium incorporation. Gram-scale reaction and further derivatization without deuterium erosion highlight the synthetic utility of this method for the formation of a wide range of isotopically labelled compounds. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2021.132211