Journal
CHEMISTRY-AN ASIAN JOURNAL
Volume 3, Issue 8-9, Pages 1517-1522Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/asia.200800135
Keywords
amines; boron; copper; cross-coupling; synthetic methods
Categories
Funding
- Global COE Program [B01]
- Ministry of Education, Culture, Sports, Science, and Technology, Japan
- [18064001]
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The N arylation of primary and secondary aliphatic amines, anilines, and imidazoles with novel potassium aryl triolborates was carried out in the presence of a reoxidant and a catalytic amount of Cu(OAc)(2) (10mol%). Aryl triolborates were found to be better reagents than aryl boronic acids or potassium aryl trifluoroborates as the former achieved high yields under mild conditions. Coupling of primary and secondary aliphatic amines to give N-aryl amines in excellent yields was performed under oxygen atmosphere. The reactions of anilines and imidazoles to provide N-aryl anilines and N-aryl imidazoles in good yields proceeded smoothly when trimethylamine N-oxide was used as an oxidant.
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