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Synthesis 2009(8): 1309-1317
DOI: 10.1055/s-0028-1088038
DOI: 10.1055/s-0028-1088038
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
Cross-Coupling Reactions of Halopurines with Aryl- and Alkyltrifluoroborates; The Scope and Limitations in the Synthesis of Modified Purines
Further Information
Received
17 December 2008
Publication Date:
25 March 2009 (online)
Publication History
Publication Date:
25 March 2009 (online)
Abstract
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.
Key words
purines - cross-coupling reactions - organotrifluoroborates - palladium - phosphine ligands
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