Cross-Coupling Reactions of Halopurines with Aryl- and Alkyltrifluoroborates; The Scope and Limitations in the Synthesis of Modified Purines

Cross-Coupling Reactions of Halopurines with Aryl- and Alkyltrifluoroborates; The Scope and Limitations in the Synthesis of Modified Purines
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DOI:
10.1055/s-0028-1088038
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发表时间:
2009-04-17
影响因子:
2.6
通讯作者:
Hocek, Michal
Hocek, Michal
中科院分区:
化学4区
文献类型:
--
作者:
Hasnik, Zbynek;Pohl, Radek;Hocek, Michal

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The scope and limitations of the use of the palladium-catalyzed cross-coupling reactions of diverse alkyl- and aryltrifluoroborates with halopurines have been studied. While aryl- and hetaryltrifluoroborates reacted readily with both 6-chloropurines and 8-bromoadenines to give the corresponding 6- or 8-aryl derivatives in high yields, the alkyltrifluoroborates were much less reactive and, even after thorough optimization, only methyl- and cyclopropyltrifluoroborates gave moderate yields of the desired alkylated purines, while other alkyl-, dialkylaminomethyl- and ethoxycarbonylethyltrifluoroborates did not give any reaction.