2009
DOI: 10.1021/ol802734f
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Copper Oxide Nanoparticle-Catalyzed Coupling of Diaryl Diselenide with Aryl Halides under Ligand-Free Conditions

Abstract: 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.

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Cited by 173 publications
(52 citation statements)
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“…Cu(0) or CuO-NPs have been employed for catalyzing the synthesis of aryl selenides because of their easy availability, less toxicity, and low cost. For instance, Reddy and coworkers 79 reported that CuO-NPs catalyzed coupling of aryl iodides with diphenyl diselenide to form diaryl selenides under ligand-free conditions in excellent yields (Scheme 6.14).…”
Section: Metal Nanoparticle-catalyzed Aryl-selenium Bond Formationmentioning
confidence: 99%
“…Cu(0) or CuO-NPs have been employed for catalyzing the synthesis of aryl selenides because of their easy availability, less toxicity, and low cost. For instance, Reddy and coworkers 79 reported that CuO-NPs catalyzed coupling of aryl iodides with diphenyl diselenide to form diaryl selenides under ligand-free conditions in excellent yields (Scheme 6.14).…”
Section: Metal Nanoparticle-catalyzed Aryl-selenium Bond Formationmentioning
confidence: 99%
“…A new, efficient, and ligand-free cross-coupling reaction of aryl halides and diaryl diselenides using catalytic amounts of nanocrystalline CuO as a catalyst and with KOH as the base in DMSO at 110 8C was reported by Rao et al [88] This procedure was utilized for the synthesis of a variety of aryl selenides in excellent yields from the readily available aryl halides and diaryl diselenides. In a preliminary experiment, when iodobenzene was treated with diphenyl diselenide in the presence of 2 mol % of CuO nanoparticles and KOH (2.0 equiv) in DMSO (2.0 mL) for 12 h, the corresponding diaryl selenide was obtained in 94 % yield (Table 25).…”
Section: Coupling Reaction Of Diaryl Diselenide and Aryl Halides Undementioning
confidence: 99%
“…CuO as a p-type semiconducting material has received considerable attention due to its wide applications in fields such as gas sensors, magnetic phase transitions, superconductors and photocatalysts [13][14][15][16][17][18][19]. Inspired by enhancement of the properties of nanoparticles through anchoring them onto graphene sheets, researchers have attempted to prepare CuO nanoparticle decorated graphene sheets.…”
Section: Introductionmentioning
confidence: 99%