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 9<i>H</i>-purin-6-yl)pyridin-2(1<i>H</i>)-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.