Copper-Catalyzed Oxirane-Opening Reaction with Aryl Iodides and Se Powder

Abstract

Using Se powder as the selenating reagent, the copper-catalyzed double C-Se cross-coupling of aryl iodides, epoxides, and elemental selenium has been developed. This strategy provides a straightforward approach to the synthesis of β-hydroxy phenylselenides with excellent regioselectivity of the ring opening reaction. This process proceeds in generally good yields and is compatible with a broad range of functional groups.

Ring opening reactions of heterocycles with selenium and tellurium nucleophiles

“…39 Wu, Liu, and co-workers reported the synthesis of β-arylseleno alcohols via a copper catalysed three-component ring opening reaction of epoxides with selenium powder and aryl iodides. 40 The methodology provides a straightforward access to a wide variety of hydroxy-substituted aryl-alkyl selenides with a good functional group tolerance (Scheme 19 Scheme 21: Proposed reaction mechanism for the synthesis of hydroxy alkynyl alkyl selenides via three-component coupling of terminal alkynes, selenium, and epoxides.…”

“…Particularly, bis(trimethylsilyl)selenide 36 -or hexamethyldisilaselenane (HMDSS), (Me 3 Si) 2 Se -behaved as a very versatile selenium transfer reagent, enabling the synthesis of different classes of organoselenium compounds upon reaction with strained heterocycles in the presence of catalytic amount of fluoride or phenolate anions. Epoxides, aziridines, and thiiranes could be selectively converted into the corresponding β-hydroxy-, β-amino-, and β-mercaptoselenides (37-39) or diselenides (40)(41)(42) just tuning the amount of (Me 3 Si) 2 Se. 53 Indeed, selenides were the exclusive reaction products observed when using an excess of the electrophile (ca.…”

Silver‐Catalyzed One‐Pot Three‐Component Selective Synthesis of β‐Hydroxy Selenides

“…Over the past decade, elemental selenium has gained considerable attention as a reagent for the introduction of linkage atoms in organic synthesis, because of its commercial availability, bench‐stability, and ease of handling. Recently, our group developed a copper‐catalyzed double C−Se cross‐coupling of aryl iodides, epoxides, and elemental selenium . However, to the best of our knowledge, transition‐metal catalyzed selective ring‐opening arylselenation of epoxides, organoboronic acids and Se powder to form new C−Se bonds has never been reported.…”

Copper‐Catalyzed Four‐Component Cascade Reaction for the Construction of Triazoles Bearing β‐Hydroxy Chalcogenides

“…[5,6] The three-component reactions of aryl iodides/aryl boronic acids, elemental selenium and epoxides have also been developed to prepare βhydroxy arylselenides. [7] However, construction of βhydroxy arylsulfides by using inorganic sulfurizing reagents has not been well-developed until now.…”