Harnessing Alkylpyridinium Salts as Electrophiles in Deaminative Alkyl–Alkyl Cross-Couplings
| Autor: | Mary P. Watson, Shane Plunkett, Samantha O. Santana, Corey H. Basch |
|---|---|
| Rok vydání: | 2019 |
| Předmět: |
Alkylation
Halide 010402 general chemistry 01 natural sciences Biochemistry Medicinal chemistry Article Catalysis Alkyl amine Electron Transport chemistry.chemical_compound Colloid and Surface Chemistry Amines Alkyl chemistry.chemical_classification Negishi coupling Stereoisomerism General Chemistry Bond formation 0104 chemical sciences Pyrimidines chemistry Electrophile Salts lipids (amino acids peptides and proteins) Derivative (chemistry) |
| Zdroj: | Journal of the American Chemical Society. 141:2257-2262 |
| ISSN: | 1520-5126 0002-7863 |
| Popis: | A Negishi cross-coupling of alkyl pyridinium salts and alkylzinc halides has been developed. This is the first example of alkyl–alkyl bond formation via cross-coupling of an alkyl amine derivative with an unactivated alkyl group, and allows both primary and secondary alkyl pyridinium salts to react with primary alkylzinc halides with high functional group tolerance. When combined with formation of the pyridinium salts from primary amines, this method enables the non-canonical transformation of NH(2) groups into a wide range of alkyl substituents with broad functional group tolerance. |
| Databáze: | OpenAIRE |
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