A general method for the formation of diaryl selenides using copper(I) catalysts

Modern Synthetic Methods for Copper‐Mediated C(aryl)O, C(aryl)N, and C(aryl)S Bond Formation

“…Recently, the introduction of copper-mediated methods for the formation of C(aryl)ÀSe bonds was demonstrated by Gujadhur and Venkataraman, who effected the Cu I -mediated cross-coupling of aryl iodides with phenylselenol. [155] The best reaction conditions involved the use of CuI (10 mol%), neocuproine, and NaOtBu (or K 2 CO 3 ) as base in toluene at 100 8C. Recently, Taniguchi and Onami showed that unsymmetrical diaryl selenides can be formed from aryl iodides and diphenyl selenides in the presence of Cu 2 O and Mg under neutral conditions.…”

Magnetically Separable and Reusable Copper Ferrite Nanoparticles for Cross‐Coupling of Aryl Halides with Diphenyl Diselenide

“…1 (3,5-Dimethylphenyl)(phenyl)selane (3e): [22] Yellowish oil (90 %, 234 mg; Table 3, Entry 5). 1 [24] Yellowish oil (74 %, 222 mg; [25] Yellowish oil (86 %, 221 mg; [16] Yellowish oil (78 %, 302 mg; Ethyl 4-(Phenylselanyl)benzoate (3u): [25] Yellowish oil (75 %, 228 mg; 2-(Phenylselanyl)thiophene (3v): [16] Yellowish oil (85 %, 203 mg; Table 3, Entry 22). 1 (Naphthalene-5-yl)(phenyl)selane (3w): [25] Yellowish oil (80 %, 227 mg; Supporting Information (see footnote on the first page of this article): Copies of the 1 H NMR and 13 C NMR spectra of all the compounds.…”

“…[15] Earlier, Cristau and co-workers reported that aryl selenides can be obtained by a cross-coupling reaction of aryl halides and sodium benzeneselenoate in the presence of a Ni IIbased catalytic system. [9] Venkataraman [16] et al explored the cross-coupling reaction of aryl iodides and diphenyl diselenide by using CuI (10 mol-%) and neocuprine as a catalyst and ligand and NaOtBu as a base in toluene at 110°C to obtain diaryl selenides in good to excellent yields. Several metals like palladium, [17] copper, [18] nickel, [9,14,19] indium, [20] and lanthanum [21] based catalysts in combination with various ligands are employed for the formation of C-Se bonds.…”

Transition metal- and solvent-free synthesis of unsymmetrical diaryl sulfides and selenides under ball-milling

“…6 Hence there has been an obvious interest towards the development of synthetic methodologies for the synthesis of these compounds. The majority of the reported protocols involved transition metals like Pd, [7][8] Cu, [9][10][11][12] Ni, [13][14][15] and Fe [16][17][18] in the reaction of aryl halides or aryl boronic acids to form chalcogenides. But few transition metal-free procedures were also reported for the reaction of aryl diazonium salts and lithium, sodium and potassium salt of arene thiolate / selenolate/ tellurolate.…”