Nickel Catalyzed Aryl–Aryl Bridging C–N Bond Activation of 2-Pyridylpyridones and 6-Purinylpyridones

A Ni-catalyzed C–N bond activation of 2-pyridylpyridone and 1-(9-alkyl 9H-purin-6-yl)pyridin-2(1H)-one and coupling with arylboronic acid have been achieved. A unique feature of this reaction is the strategic activation of the bridging C–N bond and replacement of the pyridone unit with aryl groups using nickel catalyzed Suzuki–Miyaura coupling. This provides an exciting new tool to build C–C bonds in the place of pyridones. A wide variety of substrates and boronic acids are amenable to this transformation. More importantly, we have successfully synthesized a variety of C(6)-arylated purines via deaminative cross-coupling which are very useful in developing unnatural nucleobases, nucleotides, and nucleosides.