A residue-free production of biaryls using supported gold nanoparticles

Abstract

Small gold nanoparticles in the presence of O2 are able to cleave CH bonds of non-activated arenes and facilitate catalytic formation of biaryls under mild conditions. This procedure avoids the common requirement of iodine, acids, bases, and/or other stoichiometrical additives to accomplish multiple turnovers and results in a zero-waste synthetic process. A number of unactivated arenes such as benzene, toluene, p-xylene, nitrobenzene, chlorobenzene, or phenol are selectively converted to the corresponding biaryls, with accumulated turnover numbers greater than 600. Kinetic measurements, in combination with IR, HRTEM, and STEM-HAADF data, suggest that the reaction takes place on gold atoms that are metallic in character, with the highest CC bond formation rate provided by gold nanoparticles of approximately 3nm of diameter. A radical-free reaction mechanism is postulated on the basis of the kinetic measurements. The results represent a first stone for the waste-free preparation of biaryls using supported gold catalysts.