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Rhodium(III)-catalyzed CF3-carbenoid C–H functionalization of 6-arylpurines

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Abstract

An efficient method for the CF3-carbenoid C–H functionalization of 6-arylpurines has been developed. This protocol uses readily available methyl 3,3,3-trifluoro-2-diazopropionate as a cross-coupling partner and proceeds smoothly under chelation-controlled Rh(III) catalysis. The reactions provide the corresponding carbene insertion products with high regioselectivity within a few hours and allow the introduction of both the CF3 and carboxylate functions into biologically important purine molecules including nucleoside derivatives.

Graphical abstract: Rhodium(iii)-catalyzed CF3-carbenoid C–H functionalization of 6-arylpurines

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Publication details

The article was received on 15 Mar 2018, accepted on 28 Mar 2018 and first published on 28 Mar 2018


Article type: Paper
DOI: 10.1039/C8OB00645H
Citation: Org. Biomol. Chem., 2018, Advance Article
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    Rhodium(III)-catalyzed CF3-carbenoid C–H functionalization of 6-arylpurines

    D. V. Vorobyeva, M. M. Vinogradov, Y. V. Nelyubina, D. A. Loginov, A. S. Peregudov and S. N. Osipov, Org. Biomol. Chem., 2018, Advance Article , DOI: 10.1039/C8OB00645H

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