Base-Promoted Reactions of Organostibines with Alkynes and Organic Halides to Give Chalcogenated (Z)-Olefins and Ethers

Herein, with air-stable chalcogenated stibines (Sb-ER) as organometallic chalcogenating reagents, we developed base-promoted (Z)-hydrochalcogenation of alkynes with DMSO/DMSO-d(6) as hydrogen/deuterium sources, giving chalcogenated (Z)-olefins in good yields and with excellent regioselectivity. These reagents, easily synthesized from halostibines with in situ generated [Zn(ER)(2)] at room temperature within a few minutes, could be also used in the base-promoted C(sp(3))-S(Se) cross-coupling with C(sp(3))-X and copper-catalyzed C(sp(2))-S(Se) cross-coupling with C(sp(2))-X (X = F, CI, Br, I) under mild conditions. This protocol could also be simply extended to organobismuth complexes (Bi-ER) with good functional tolerance.

Automated summary

Here, we developed a method for synthesizing chalcogenated olefins using air-stable chalcogenated stibines as organometallic chalcogenating reagents. In addition, these reagents can also be used for C-S cross-coupling reactions and copper-catalyzed olefin chalcogenation reactions, and can be easily extended to organobismuth complexes.