Transition metal free C(sp³)-C(sp³) coupling between alcohols and N-heteroarenes via a dehydrogenative SET/HAT process

Transition metal free direct activation and Csp(3)-Csp(3) coupling of benzylic alcohol derivatives with N-heteroarenes was performed in a basic medium in the presence of an aryl halide additive. Various E-alkenyl heteroarenes were obtained, among which is the STB-8 imaging reagent of beta-amyloid associated with Alzheimer's disease. From the combination of experimental results and DFT calculations, we assume that the reaction proceeds via a combined SET/HAT dehydrogenation pathway.