Issue 31, 2013
From the journal:

Organic & Biomolecular Chemistry

Direct C–H sulfenylation of purines and deazapurines†

Martin Klečka,ab   Radek Pohl,b   Jan Čejkab  and  Michal Hocek*ab  

* Corresponding authors

a Department of Organic Chemistry, Faculty of Science, Charles University in Prague, Hlavova 8, CZ-12843 Prague 2, Czech Republic

b Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Gilead & IOCB Research Center, Flemingovo nam. 2, CZ-16610 Prague 6, Czech Republic
E-mail: hocek@uochb.cas.cz

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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Article information

DOI
https://doi.org/10.1039/C3OB40881G
Article type
Paper
Submitted
29 Apr 2013
Accepted
11 Jun 2013
First published
12 Jun 2013
This article is Open Access

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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