期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 74, 期 24, 页码 9517-9520出版社
AMER CHEMICAL SOC
DOI: 10.1021/jo902124c
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资金
- Marie Curie Research Training Network 'REVCAT'
A methodology that affords N-alkyl-2-arylpyrroles and N-aryl-2-arylpyrroles via direct coupling from aryl iodides has been developed. After examining various reaction parameters: solvent, ratio of reagents, catalyst, base and additives the optimal conditions for the condensation were identified. Two crucial factors, (a) anhydrous DMSO as solvent and (b) 5 M excess of pyrrole counterpart, were found to strongly influence the reaction outcome. The conditions identified (PdCl2(PPh3)(2), AgOAc, anhyd DMSO, KF, 100 degrees C, 5 h) resulted in the formation of 2-arylpyrroles in 14-80% yield. Furthermore, the synthesis is compatible with electron-withdrawing and electron-donating groups on the aryl moiety.
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