Copper‐Promoted N‐Arylation of the Imidazole Side Chain of Protected Histidine by Using Triarylbismuth Reagents
| Autor: | Alexandre Gagnon, Hwai‐Chien Chan, Bianca Bueno, Adrien Le Roch |
|---|---|
| Rok vydání: | 2021 |
| Předmět: |
010405 organic chemistry
Aryl Organic Chemistry Imidazoles chemistry.chemical_element General Chemistry 010402 general chemistry 01 natural sciences Copper Medicinal chemistry Catalysis 3. Good health 0104 chemical sciences chemistry.chemical_compound chemistry Reagent Functional group Side chain Imidazole Histidine Indicators and Reagents Dichloromethane |
| Zdroj: | Chemistry – A European Journal. 27:13330-13336 |
| ISSN: | 1521-3765 0947-6539 |
| Popis: | The N-arylation of the side chain of histidine by using triarylbismuthines is reported. The reaction is promoted by copper(II) acetate in dichloromethane at 40 °C under oxygen in the presence of diisopropylethylamine and 1,10-phenanthroline and allows the transfer of aryl groups with substituents at any position of the aromatic ring. The reaction shows excellent functional group tolerance and is applicable to dipeptides where the histidine is located at the N terminus. A histidine-guided backbone N-H arylation was observed in dipeptides where the histidine occupies the C terminus. |
| Databáze: | OpenAIRE |
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