Pd/Cu-Catalyzed Cross-Coupling of Bis(2-bromovinyl) Selenides with Terminal Acetylenes: Unusual Involvement of Selanyl Function in the Sonogashira Reaction

Abstract

The Pd/Cu-catalyzed Sonogashira reaction of (E,E)-bis(2-bromovinyl) selenide and (E,E)-bis(1-bromo-1-hexen-2-yl) selenide with terminal alkynes was found to proceed at room temperature involving both bromine atoms and the selanyl function. As a result, new bis-(1,3-enynyl) selenides and enediyne hydrocarbons are formed with a complete retention of the stereoconfiguration of the initial selenides. Due to steric hindrances in the cross-coupling at the selenyl function in the case of (E,E)-bis(1-bromo-1-hexen-2-yl) selenide, the second process is realized to a lesser extent than with unsubstituted (E,E)-bis(2-bromovinyl) selenide.

Keywords

• 2-bromovinyl selenides
• cross-coupling
• palladium catalyst
• terminal acetylenes
• endiynes
• bis-(enynyl) selenides