title: Solvent-controlled halo-selective selenylation of aryl halides catalyzed by Cu(II) supported on Al2O3. A general protocol for the synthesis of unsymmetrical organo mono- and bis-selenides.
abstract: Alumina-supported Cu(II) efficiently catalyzes selenylation of aryl iodides and aryl bromides by diaryl, dialkyl, and diheteroaryl diselenides in water and PEG-600, respectively, leading to a general route toward synthesis of unsymmetrical diaryl, aryl-alkyl, aryl-heteroaryl, and diheteroaryl selenides. A sequential reaction of bromoiodobenzene with one diaryl/diheteroaryl/dialkyl diselenide in water and another diaryl/diheteroaryl/dialkyl diselenide in PEG-600 in the second step produces unsymmetrical diaryl, diheteroaryl, or aryl-alkyl bis-selanyl benzene. A library of functionalized organo mono- and bis-selenides, including a potent biologically active molecule and a couple of analogues of bioactive selenides, were obtained in high yields by this protocol. The reactions are chemoselective and high yielding. The Cu-Al2O3 catalyst is recycled for seven runs without any appreciable loss of activity.
authors.affiliation: Department of Organic Chemistry, Indian Association for the Cultivation of Science, Jadavpur, Kolkata 700032, India.
authors.forename: Tanmay
authors.initials: T
authors.lastname: Chatterjee
authors.forename: Brindaban C
authors.initials: BC
authors.lastname: Ranu
mesh_terms: D000537:Aluminum Oxide / Q000737:chemistry*; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D006846:Hydrocarbons, Halogenated / Q000737:chemistry*; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D012643:Selenium / Q000737:chemistry*; D012997:Solvents / Q000737:chemistry
chemical_list: D006846:Hydrocarbons, Halogenated; D009942:Organometallic Compounds; D012997:Solvents; D003300:Copper; D012643:Selenium; D000537:Aluminum Oxide