Copper- and Cobalt-Catalyzed Syntheses of Thiophene-Based Tertiary Amines

Autor: Bouarfa, Salima, Graβl, Simon, Ivanova, Maria, Langlais, Timothy, Bentabed-Ababsa, Ghenia, Lassagne, Frédéric, Erb, William, Roisnel, Thierry, Dorcet, Vincent, Knochel, Paul, Mongin, Florence
Přispěvatelé: Institut des Sciences Chimiques de Rennes (ISCR), Université de Rennes (UR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Ludwig-Maximilians-Universität München (LMU), Université d'Oran 1 Ahmed Ben Bella [Oran], Institut de Chimie des Substances Naturelles (ICSN), Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Ludwig Maximilian University [Munich] (LMU), Conseil National de la Recherche Scientifique, None, Université de Rennes 1, None, European Regional Development Fund, None, Alexander von Humboldt-Stiftung, NONE, Thermofisher, Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Rennes 1 (UR1), Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées (INSA), Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)
Jazyk: angličtina
Rok vydání: 2019
Předmět:
Zdroj: European Journal of Organic Chemistry
European Journal of Organic Chemistry, 2019, 2019 (20), pp.3244-3258. ⟨10.1002/ejoc.201900276⟩
European Journal of Organic Chemistry, Wiley-VCH Verlag, 2019, 2019 (20), pp.3244-3258. ⟨10.1002/ejoc.201900276⟩
ISSN: 1434-193X
1099-0690
Popis: International audience; Thienylzinc halides and related compounds prepared by deprotonation followed by transmetalation were used in copper-catalyzed amination using N-benzoyloxy secondary amines. By extending the reaction to 1,5-naphthyridine, it was showed that the competitive dimer formation observed in the case of thiophenes was linked with the low stability of some thienylamines rather than homocoupling. Interestingly, thienylzinc halides and related compounds prepared by transmetalation of thienylmagnesium halides, either prepared from their bromo-precursors or generated by deprotometalation, were satisfactorily employed in cobalt-catalyzed aminations. Finally, aminothiophenes were involved in copper-catalyzed mono-and diN -arylations, affording differently substituted di-and triphenylamines.
Databáze: OpenAIRE
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