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Issue 31, 2013
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Direct C–H sulfenylation of purines and deazapurines

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Abstract

A general method for Cu-catalyzed C–H sulfenylation of purines, 7-deaza- and 9-deazapurines with aryl- or alkyldisulfides has been developed. In purines, the reaction occurs at position 8, in 7-deazapurines at position 7 and in 9-deazapurines at position 9, leading to new interesting arylsulfanyl derivatives of purine or deazapurine bases. The resulting 8-arylsulfanylpurines undergo Liebesking–Srogl coupling with arylstannanes or boronic acids, whereas the (arylsulfanyl)deazapurines are not reactive under these conditions.

Graphical abstract: Direct C–H sulfenylation of purines and deazapurines

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Publication details

The article was received on 29 Apr 2013, accepted on 11 Jun 2013 and first published on 12 Jun 2013


Article type: Paper
DOI: 10.1039/C3OB40881G
Citation: Org. Biomol. Chem., 2013,11, 5189-5193
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    Direct C–H sulfenylation of purines and deazapurines

    M. Klečka, R. Pohl, J. Čejka and M. Hocek, Org. Biomol. Chem., 2013, 11, 5189
    DOI: 10.1039/C3OB40881G

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