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Preparation of Functionalized Amides Using Dicarbamoylzincs.

ABSTRACT: We report a new convenient preparation of dicarbamoylzincs of type (R¹ R² NCO)₂ Zn by the treatment of ZnCl₂ and formamides R¹ R² NCHO with LiTMP in THF (15 °C, 15 min) or by the reaction of formamides R¹ R² NCHO with TMP₂ 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.

SUBMITTER: Djukanovic D

PROVIDER: S-EPMC9401601 | biostudies-literature | 2022 Aug

REPOSITORIES: biostudies-literature

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Preparation of Functionalized Amides Using Dicarbamoylzincs.

Djukanovic Dimitrije D Ganiek Maximilian A MA Nishi Kohei K Karaghiosoff Konstantin K Mashima Kazushi K Knochel Paul P

Angewandte Chemie (International ed. in English) 20220613 31

We report a new convenient preparation of dicarbamoylzincs of type (R1 R2 NCO)2 Zn by the treatment of ZnCl2 and formamides R1 R2 NCHO with LiTMP in THF (15 °C, 15 min) or by the reaction of formamides R1 R2 NCHO with TMP2 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, alken ...[more]

PMID: 35561099

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