Preparation of Functionalized Amides Using Dicarbamoylzincs

Djukanovic, Dimitrije; Ganiek, Maximilian A.; Nishi, Kohei; Karaghiosoff, Konstantin; Mashima, Kazushi and Knochel, Paul (2022): Preparation of Functionalized Amides Using Dicarbamoylzincs. In: Angewandte Chemie International Edition, Vol. 61, No. 31

Abstract

We report a new convenient preparation of dicarbamoylzincs of type ((RRNCO)-R-1-N-2)(2)Zn by the treatment of ZnCl2 and formamides (RRNCHO)-R-1-N-2 with LiTMP in THF (15 degrees C, 15 min) or by the reaction of formamides (RRNCHO)-R-1-N-2 with TMP2Zn (25 degrees 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. C-13 NMR characterization of these new carbamoylzinc derivatives is reported.

• Item Type: Journal article
• Faculties: Chemistry and Pharmacy > Department of Chemistry
• Subjects: 500 Science > 540 Chemistry
• ISSN: 1433-7851
• Language: English
• DFG: Gefördert durch die Deutsche Forschungsgemeinschaft (DFG) - 491502892