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
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author Djukanovic, Dimitrije
Ganiek, Maximilian A.
Nishi, Kohei
Karaghiosoff, Konstantin
Mashima, Kazushi
Knochel, Paul
author_facet Djukanovic, Dimitrije
Ganiek, Maximilian A.
Nishi, Kohei
Karaghiosoff, Konstantin
Mashima, Kazushi
Knochel, Paul
author_sort Djukanovic, Dimitrije
collection PubMed
description 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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spelling pubmed-94016012022-08-26 Preparation of Functionalized Amides Using Dicarbamoylzincs Djukanovic, Dimitrije Ganiek, Maximilian A. Nishi, Kohei Karaghiosoff, Konstantin Mashima, Kazushi Knochel, Paul Angew Chem Int Ed Engl Communications 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. John Wiley and Sons Inc. 2022-06-13 2022-08-01 /pmc/articles/PMC9401601/ /pubmed/35561099 http://dx.doi.org/10.1002/anie.202205440 Text en © 2022 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH https://creativecommons.org/licenses/by/4.0/This is an open access article under the terms of the http://creativecommons.org/licenses/by/4.0/ (https://creativecommons.org/licenses/by/4.0/) License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
spellingShingle Communications
Djukanovic, Dimitrije
Ganiek, Maximilian A.
Nishi, Kohei
Karaghiosoff, Konstantin
Mashima, Kazushi
Knochel, Paul
Preparation of Functionalized Amides Using Dicarbamoylzincs
title Preparation of Functionalized Amides Using Dicarbamoylzincs
title_full Preparation of Functionalized Amides Using Dicarbamoylzincs
title_fullStr Preparation of Functionalized Amides Using Dicarbamoylzincs
title_full_unstemmed Preparation of Functionalized Amides Using Dicarbamoylzincs
title_short Preparation of Functionalized Amides Using Dicarbamoylzincs
title_sort preparation of functionalized amides using dicarbamoylzincs
topic Communications
url 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
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