Preparation of Functionalized Amides Using Dicarbamoylzincs

We report a new convenient preparation of dicarbamoylzincs of type (R(1)R(2)NCO)(2)Zn by the treatment of ZnCl(2) and formamides R(1)R(2)NCHO with LiTMP in THF (15 °C, 15 min) or by the reaction of formamides R(1)R(2)NCHO with TMP(2)Zn (25 °C, 16 h). This second method tolerates sensitive groups suc...

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Detalles Bibliográficos
Autores principales: Djukanovic, Dimitrije, Ganiek, Maximilian A., Nishi, Kohei, Karaghiosoff, Konstantin, Mashima, Kazushi, Knochel, Paul
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2022
Materias:
Communications
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9401601/
https://www.ncbi.nlm.nih.gov/pubmed/35561099
http://dx.doi.org/10.1002/anie.202205440
Descripción
Sumario:We report a new convenient preparation of dicarbamoylzincs of type (R(1)R(2)NCO)(2)Zn by the treatment of ZnCl(2) and formamides R(1)R(2)NCHO with LiTMP in THF (15 °C, 15 min) or by the reaction of formamides R(1)R(2)NCHO with TMP(2)Zn (25 °C, 16 h). This second method tolerates sensitive groups such as an ester, ketone or nitro function. Reaction of these dicarbamoylzincs with allylic, benzylic, aryl, alkenyl bromides, acid chlorides, aldehydes or enones provided various polyfunctional amides in 47–97 % yields. (13)C NMR characterization of these new carbamoylzinc derivatives is reported.

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