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Ruthenium-Mediated N-Arylation for DNA-Encoded Libraries
Suraj Kanoo1,2, Eduardo de Pedro Beato1, Tim Schulte1
1Max-Planck-Institut für Kohlenforschung, D-45470 Mülheim an der Ruhr, Germany.
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C-N cross coupling reactions are widely employed for the construction of carbon-nitrogen bonds. However, control of chemoselectivity in the presence of the amino functionality in oligonucleotides remains a challenge. Here, we report the development of a new ruthenium reagent that enables the chemoselective N-arylation of amine-DNA conjugates with distinct chemoselectivity when compared to conventional palladium-based C-N bond-forming catalysts. The ruthenium reagent activates commercially available haloarenes in situ via η6 π-arene coordination for subsequent SNAr with the amine. The method is compatible with various commercially available haloarenes and aliphatic amines, and the reaction proceeds under mild conditions.
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