An efficient ligand-free C-S cross-coupling of aryl halides with aromatic/alkyl thiols has been developed using a catalytic amount of nanocrystalline indium oxide as a recyclable catalyst with KOH as the base in DMSO at 135 degrees C. A variety of aryl sulfides can be synthesized in excellent yields utilizing this protocol.

A new, efficient and ligand-free cross-coupling reaction of aryl halides and diaryl diselenides using a catalytic amount of nanocrystalline CuO as a recyclable catalyst with KOH as the base in DMSO at 110 degrees C is reported. This protocol has been utilized for the synthesis of a variety of aryl selenides in excellent yields from the readily available aryl halides and diaryl diselenides.

This work reports a cobalt(II)/ N-hydroxyphthalimide (NHPI)-catalyzed cross-dehydrogenative oxidative coupling of N-aryl tetrahydroisoquinolines with various pro-nucleophiles, such as indoles, nitroalkanes, and trialkylphosphites, active methylene compounds, and other nucleophiles, such as cyanide (ethyl cyanoformate), at room temperature under aerobic conditions. The present protocol is operationally simple and can be carried out without photoirradiation and under peroxide-free conditions, even on a gram scale, to afford the products in good to excellent yields. On the basis of mass spectrometry and control experiments, a catalytic reaction pathway has been proposed.

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Selenourea is used as an effective selenium surrogate in the C-Se cross-coupling reaction catalyzed by copper oxide nanoparticles under ligand free conditions. This protocol has been utilized for the synthesis of a variety of symmetrical diaryl selenides in good to excellent yields from the readily available aryl halides/boronic acids.