Cu(II)-mediated oxidative dimerization of 2-phenylpyridine derivatives

A Cu(II)/I₂-mediated C-H bond activation is described. A variety of 2-phenylpyridine derivatives are oxidatively dimerized at the ortho-position of the phenyl ring in which a net loss of two hydrogen atoms results in the formation of a biaryl compound via a double C-H activation/C-C bond-forming process. Moderate functional group tolerance was observed on both the aryl and the pyridyl rings. A single electron transfer (SET) or electrophilic metalation process for iodination followed by Ullmann coupling of the intermediate iodinated product is proposed as the operating mechanism for the dimerization process.