Nickel-Catalyzed Suzuki–Miyaura Coupling of Aliphatic Amides
| Autor: | Neil K. Garg, Junyong Kim, Timothy B. Boit, Nicholas A. Weires |
|---|---|
| Rok vydání: | 2018 |
| Předmět: |
chemistry.chemical_classification
Ketone 010405 organic chemistry Chemistry chemistry.chemical_element Substrate (chemistry) Sequence (biology) General Chemistry 010402 general chemistry 01 natural sciences Combinatorial chemistry Article Catalysis 0104 chemical sciences Stereocenter Nickel chemistry.chemical_compound Amide Electrophile |
| Zdroj: | ACS Catalysis. 8:1003-1008 |
| ISSN: | 2155-5435 |
| Popis: | We report the Ni-catalyzed Suzuki–Miyaura coupling of aliphatic amide derivatives. Prior studies have shown that aliphatic amide derivatives can undergo Ni-catalyzed carbon–heteroatom bond formation but that Ni-mediated C–C bond formation using aliphatic amide derivatives has remained difficult. The coupling disclosed herein is tolerant of considerable variation with respect to both the amide-based substrate and the boronate coupling partner and proceeds in the presence of heterocycles and epimerizable stereocenters. Moreover, a gram-scale Suzuki–Miyaura coupling/Fischer indolization sequence demonstrates the ease with which unique polyheterocyclic scaffolds can be constructed, particularly by taking advantage of the enolizable ketone functionality present in the cross-coupled product. The methodology provides an efficient means to form C–C bonds from aliphatic amide derivatives using nonprecious-metal catalysis and offers a general platform for the heteroarylation of aliphatic acyl electrophiles. |
| Databáze: | OpenAIRE |
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