Direct Aminoalkylation of Arenes, Heteroarenes, and Alkenes via Ni-Catalyzed Negishi Cross-Coupling Reactions
| Autor: | Paul Knochel, Laurin Melzig, Andrey Gavryushin, Teresa Dennenwaldt |
|---|---|
| Rok vydání: | 2011 |
| Předmět: |
Alkylation
Alkenes 010402 general chemistry 01 natural sciences Medicinal chemistry Catalysis Coupling reaction chemistry.chemical_compound Alkaloids Heterocyclic Compounds Nickel Organic chemistry Molecular Structure Hydrocarbons Halogenated 010405 organic chemistry Negishi coupling Aryl Organic Chemistry Total synthesis Stereoisomerism 0104 chemical sciences Cross-Linking Reagents chemistry Electrophile Quinolines Indicators and Reagents Amine gas treating Piperidine |
| Zdroj: | The Journal of Organic Chemistry. 76:8891-8906 |
| ISSN: | 1520-6904 0022-3263 |
| DOI: | 10.1021/jo201630e |
| Popis: | A room-temperature Ni-catalyzed cross-coupling of aryl, heteroaryl, and alkenyl electrophiles with aminoalkylzinc bromides, readily available from the corresponding aminoalkyl chlorides via Grignard reagents, was developed. The reaction allows a convenient one-step preparation of various aminoalkyl products, including piperidine and tropane derivatives. Such functionalized amine moieties are widely present in various biologically active molecules. Aryl, heteroaryl, and alkenyl iodides, bromides, chlorides and triflates are suitable electrophiles. A short total synthesis of two natural products, (±)-galipinine and (±)-cusparine, is also reported. |
| Databáze: | OpenAIRE |
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