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

Literature Information

Publication Date 2018-03-28
DOI 10.1039/C8OB00645H
Impact Factor 3.876
Authors

Daria V. Vorobyeva, Mikhail M. Vinogradov, Yulia V. Nelyubina, Dmitry A. Loginov, Alexander S. Peregudov, Sergey N. Osipov


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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.

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DOI: 10.1039/C7CP90120H

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Organic & Biomolecular Chemistry

Organic & Biomolecular Chemistry
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Organic & Biomolecular Chemistry (OBC) publishes original and high impact research and reviews in organic chemistry. We welcome research that shows new or significantly improved protocols or methodologies in total synthesis, synthetic methodology or physical and theoretical organic chemistry as well as research that shows a significant advance in the organic chemistry or molecular design aspects of chemical biology, catalysis, supramolecular and macromolecular chemistry, theoretical chemistry, mechanism-oriented physical organic chemistry, medicinal chemistry or natural products. Articles published in the journal should report new work which makes a highly-significant impact in the field. Routine and incremental work is generally not suitable for publication in the journal. More details about key areas of our scope are below. In all cases authors should include in their article clear rationale for why their research has been carried out.

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