Unexpected C−Se Cross-Coupling Reaction: Copper Oxide Catalyzed Synthesis of Symmetrical Diaryl Selenides via Cascade Reaction of Selenourea with Aryl Halides/Boronic Acids

• Published in: Journal of organic chemistry Vol. 75; no. 24; pp. 8720 - 8723
• Main Authors: Reddy, V. Prakash, Kumar, A. Vijay, Rao, K. Rama
• Format: Journal Article
• Language: English
• Published: Washington, DC American Chemical Society 17-12-2010
• Subjects: Boronic Acids - chemistry; Catalysis; Chemistry; Exact sciences and technology; Hydrocarbons, Halogenated - chemistry; Ligands; Magnetic Resonance Spectroscopy; Molecular Structure; Noncondensed benzenic compounds; Organic chemistry; Organoselenium Compounds - chemical synthesis; Organoselenium Compounds - chemistry; Preparations and properties; Selenium Compounds - chemical synthesis; Selenium Compounds - chemistry; Urea - analogs & derivatives; Urea - chemical synthesis; Urea - chemistry; Organic selenide; Catalytic reaction; Nanoparticle; Haloarene; Chemical coupling; Cross reaction; Boron Organic compounds; Selenium; Copper oxide; Chemical synthesis; Selenoureas; Boronic acids; Halogen Organic compounds; Successive reaction
• ISSN: 0022-3263; 1520-6904
• DOI: 10.1021/jo102017g

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.