Solution-Phase Synthesis of Diaryl Selenides Using Polymer-Supported Borohydride

Abstract

[reaction: see text] A new series of selenium-containing diaryl retinoids have been prepared by a new direct nickel(II)-catalyzed coupling of a diselenide with an iodoaryl in the presence of polymer-supported borohydride.

Aryl Carbon–Heteroatom Coupling Reactions Using Nanometal Catalyst

“…Traditionally, aryl selenides were prepared by the reaction of halobenzenes with phenyl selenol (PhSeH) or benzene selenoate anion (PhSeNa) or diphenyl diselenide (PhSeSePh) in the presence of a transition metal catalyst, for example, Pd, [47][48][49][50] Ni, 51,52 Cu salt, [53][54][55][56][57][58][59][60][61][62][63] and In. 64,65,[66][67][68][69][70][71] Diphenyl selenides can also be achieved by the transition metal-free reaction of sodium selenide and aryl diazonium salts.…”

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

“…[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.…”

Iron‐Catalyzed Ligand‐Free Carbon‐Selenium (or Tellurium) Coupling of Arylboronic Acids with Diselenides and Ditellurides

“…However, the method is limited to alkyl halides. [9,10] Meanwhile, in the metal-catalyzed chalcogenylation of aryl halides with dichalcogenide used as reactant, an efficient reductant is necessary for the generation of the corresponding anion [11] or metal-monochalcogenide complex. [12] Organoboronic acids are widely used as reagents in organic synthesis because they are commercially available, stable, generally non-toxic, and compatible with a variety of functional groups.…”