C–H Bond Alkylation of Cyclic Amides with Maleimides via a Site-Selective-Determining Six-Membered Ruthenacycle
| Autor: | Thierry Roisnel, Rafael Gramage-Doria, Marion Goujon, Christian Bruneau, Yu-Chao Yuan |
|---|---|
| Přispěvatelé: | Institut des Sciences Chimiques de Rennes (ISCR), 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), Agence Nationale de la Recherche, CA15106, European Cooperation in Science and Technology, Centre National de la Recherche Scientifique, China Scholarship Council, Université de Rennes 1, Rennes Metropole, 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) |
| Rok vydání: | 2019 |
| Předmět: |
C h bond
[CHIM.ORGA]Chemical Sciences/Organic chemistry 010405 organic chemistry Stereochemistry Site selectivity education Organic Chemistry [CHIM.CATA]Chemical Sciences/Catalysis Alkylation 010402 general chemistry 01 natural sciences 0104 chemical sciences chemistry.chemical_compound A-site chemistry Amide Functional group Surface modification Maleimide |
| Zdroj: | Journal of Organic Chemistry Journal of Organic Chemistry, American Chemical Society, 2019, 84 (24), pp.16183-16191. ⟨10.1021/acs.joc.9b02690⟩ Journal of Organic Chemistry, 2019, 84 (24), pp.16183-16191. ⟨10.1021/acs.joc.9b02690⟩ |
| ISSN: | 1520-6904 0022-3263 |
| DOI: | 10.1021/acs.joc.9b02690 |
| Popis: | International audience; The first example of a ruthenium-catalyzed C–H bond alkylation via six-membered ruthenacycles is presented. This is disclosed for the C–H bond alkylation of biologically relevant cyclic amides with maleimide derivatives. The cyclic tertiary amide core acted as a directing group (DG) enabling formation of six-membered cycloruthenated species responsible for the control of the regio- and site selectivity of the reaction as well as the excellent functional group tolerance. Unexpectedly, cyclic amides were found to be better DGs than pyridine-containing ones or cyclic imides for this type of C–H bond functionalization. |
| Databáze: | OpenAIRE |
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