Catalytic alkylation of methyl-N-heteroaromatics with alcohols.

A novel catalytic C-C coupling reaction in which N-heteroaromatic-substituted methyl groups are efficiently alkylated using primary alcohols is introduced. The synthesis protocol is based on iridium catalysts and most likely relies on the "borrowing hydrogen" or "hydrogen autotransfer" mechanism. A variety of substrate combinations can readily be employed in this reaction, including pyrimidines, pyrazines, pyridazines, and even fairly activated 2- and 4-picolines.