Synthesis of aryl phenyl and heteroaryl phenyl selenides by nickel(II)-catalyzed arylation of sodium benzeneselenolate

A Highly Efficient Method for the Copper‐Catalyzed Selective Synthesis of Diaryl Chalcogenides from Easily Available Chalcogen Sources

“…[3] To overcome these drawbacks, transition-metal-catalyzed cross-couplings of thiols with aryl halides have been explored. [1e,3a,4] Nickel, [5] palladium, [6] copper, [7,8] iron, [9] and cobalt catalysts [10] have recently emerged as appealing catalysts for this reaction, but these metal-catalyzed reactions require readily oxidizable, foul-smelling, expensive, and less available arene chalcogens.…”

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

“…[8] Diaryl selenides can also be prepared by the reaction of aryl/alkyl metal selenoates with aryl halides, [9] the reaction of organometallic compounds like aryllithiums and arylmercurials with selenium dications, [10] and the reduction of diselenides by metals to monoselenides. [11] However, the existing synthetic protocols have limited scope due to lengthy synthetic sequences, often requiring 120°C.…”

“…[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.…”

“…[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. However, these metal-catalyzed reactions involve the addition of well-designed ligands and well-defined catalysts, require longer reaction times, and provide lower yields, which may increase the cost and limit the scope of applications.…”

Zinc-Mediated Synthesis of Diaryl Selenides from Diaryl Diselenides and Diaryliodonium Salts in Aqueous Media

“…Diaryl selenides, containing amino groups, have useful antioxidative properties [2], and some biologically active molecules include diarylselenium moiety [3]. Among the useful and general methods for the preparation of symmetrical and unsymmetrical diaryl selenides, we can cite those involving the treatment of arenediazonium salts with sodium selenide [4] and with sodium benzeneselenolate [5], the reaction of electrophilic selenium species such as diselenides and selenocyanates with Grignard reagents and aryllithiums [6], the arylation of sodium benzeneselenolate with an aryl halide catalyzed by nickel (II) complex [7], photochemical reaction of simple haloarenes with sodium areneselenolate [8], the reaction of diaryl diselenides with activated halides in the presence of aminoiminomethanesulfinic acid [9], copper-catalyzed reaction of aryl iodide and diphenyl diselenide using magnesium metal [10], palladium-catalyzed reactions of phenyltributylstannyl selenide (PhSeSnBu 3 ) with aryl halides and triflates [11]. However, some of these methods suffer from disadvantages such as the use of toxic, hazardous, expensive or less easily available reagents, harsh reaction conditions or lower yields.…”