A Stereoselective Synthesis of (E)-Arylvinyl Selenides via Coupling of (E)-Vinylseleno Zirconocenes and Diaryliodonium Salts

Electrochemical preparation of α,α′-dicarbonylselenides

“…Allyl selenides have been synthesized via the reaction of allylbromide with diselenides promoted by the Sm -BiCl 3 system in aqueous media 23 and (E)-arylvinylselenides were prepared by coupling of (E)-vinylselenozirconocenes and diaryliodonium salts. 24 In the present paper we describe the synthesis of a,a 0 -dicarbonylselenides by reaction of electrogenerated enolates over a-carbonylselenocyanates.…”

The synthesis of thiols, selenols, sulfides, selenides, sulfoxides, selenoxides, sulfones and selenones

“…90 A stereoselective synthesis of (E)-aryl vinyl selenides via the reaction of elemental selenium with vinyl zirconocenes has been reported. 91 The palladium-catalysed coupling of the intermediate vinylselenozirconocenes with diaryliodonium salts gives (E)-aryl vinyl selenides in good yield (Scheme 58). 91 In a related study, (E)-α-selenylvinylzirconiums formed by the hydrozirconation of alkynyl selenides, have been found to undergo copper-catalysed carbonylative cross-coupling with alkynyliodonium tosylates (Scheme 59).…”

“…91 The palladium-catalysed coupling of the intermediate vinylselenozirconocenes with diaryliodonium salts gives (E)-aryl vinyl selenides in good yield (Scheme 58). 91 In a related study, (E)-α-selenylvinylzirconiums formed by the hydrozirconation of alkynyl selenides, have been found to undergo copper-catalysed carbonylative cross-coupling with alkynyliodonium tosylates (Scheme 59). 92 (Z)-Selenyl-α,β-unsaturated ketones have also been prepared by the palladium-catalysed cross-coupling of (E)-α-selenylvinylstannanes with acyl halides.…”

insertion of Selenium into Zinc Carbon Bonds and Its Application in the synthesis of Unsymmetrical Diarylselenides

“…Xin-Hua Xu, 1 * and Wen-Qi Liu 2 1 College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082, China, 2 Department of Chemistry of Chenzhou Teacher College, ChenZhou 423000, China…”

“…There are many reports every year about their preparation and reaction. [1][2][3][4][5][6] A convenient and general method of introducing a selenium group into organic molecules is the reaction of a metal selenoate with an appropriate electrophile. Recently selenoates or complexes of transition metal such as Ti 7 , Zr 8 , Hf 9 , Sm 10 , Yb 11 and Cd 12 have been used in the synthesis of organoselenium compounds.…”