Scope and Limitations of the Palladium-Catalyzed Direct 1,2-Diheteroarylation of 1,2-Dihalobenzene Derivatives
| Autor: | Henri Doucet, Linhao Liu |
|---|---|
| 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), Centre National de la Recherche Scientifique (CNRS), Universite de Rennes 1, China Scholarship Council (CSC) |
| Rok vydání: | 2022 |
| Předmět: | |
| Zdroj: | Synthesis: Journal of Synthetic Organic Chemistry Synthesis: Journal of Synthetic Organic Chemistry, 2022, ⟨10.1055/a-1981-3213⟩ |
| ISSN: | 1437-210X 0039-7881 |
| DOI: | 10.1055/a-1981-3213 |
| Popis: | The reactivity of 1,2-dihalobenzenes in palladium-catalyzed C–H bond functionalization is more difficult to control than that of 1,3- and 1,4-dihalobenzenes because of a possible Pd 1,4-migration during the second catalytic cycle. With C3-substituted heteroarenes this 1,4-palladium migration is not possible and the reaction allows the synthesis of a wide variety of functionalized 1,2-heteroarylated benzene derivatives in high yields. Conversely, only a few heteroarenes with a free C3 position, such as thiazoles, furans and imidazoles, allow the preparation of 1,2-heteroarylated benzenes. Despite these limitations, this one-pot procedure employing an easily available catalyst [Pd(OAc)2] and an inexpensive base (KOAc) provides a very simple method for the preparation of several 1,2-heteroarylated benzenes. |
| Databáze: | OpenAIRE |
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