Iron-Catalyzed Coupling of Methyl N-Heteroarenes with Primary Alcohols: Direct Access to E-Selective Olefins

An efficient Fe-catalyzed system is reported for direct alpha-olefination of methyl-substituted N-heteroarenes with primary alcohols. The catalytic dehydrogenative coupling enables a series of functionalized E-olefinated N-heteroaromatics with excellent selectivity (>99%). Initial mechanistic studies including deuterium-labeling experiments provide evidence for the participation of the benzylic C-H/D bond of alcohols.