A simple and efficient protocol to prepare divinyl selenides has been developed by the regio- and stereoselective addition of sodium selenide species to aryl alkynes. The nucleophilic species was generates in situ, from the reaction of elemental selenium with NaBH4, utilizing PEG-400 as the solvent. Several divinyl selenides were obtained in moderate to excellent yields with selectivity for the (Z,Z)-isomer by a one-step procedure that was carried out at 60 °C in short reaction times. The methodology was extended to tellurium, giving the desired divinyl tellurides in good yields. Furthermore, the Fe-catalyzed cross-coupling reaction of bis(3,5-dimethoxystyryl) selenide 3f with (4-methoxyphenyl)magnesium bromide 5 afforded resveratrol trimethyl ether 6 in 57% yield.
Recent outstanding advances in the C–Se bond formation through transition metalcatalysed direct selanylation, providing new insights into their mechanistic aspects, were provided in this perspective.
A convenient synthesis of 1‐(2‐organylchalcogenylethynyl)‐2‐butylselenanylbenzenes was established taking advantage of the selective reaction of 1‐(2,2‐dibromovinyl)‐2‐butylselenanylbenzenes with thiols or diorganyl diselenides. The new 1‐(2‐chalcogenylethynyl)‐2‐butylselenanylbenzenes were prepared in good yields and used as precursors of 2‐organylchalcogenylbenzo[b]selenophenes via electrophilic cyclization using I2, Br2 or PhSeBr as electrophiles. Different classes of new 3‐substituted‐ (3‐iodo, 3‐bromo, 3‐phenylselenanyl) benzo[b]selenophenes were prepared in good yields. The synthetic application of the obtained products was demonstrated employing the benzo[b]selenophenes in Suzuki and Sonogashira cross‐coupling reactions.
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