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Herein, with air-stable chalcogenated stibines (Sb-ER) as organometallic chalcogenating reagents, we developed base-promoted (Z)-hydrochalcogenation of alkynes with DMSO/DMSO-d6 as hydrogen/deuterium sources, giving chalcogenated (Z)-olefins in good yields and with excellent… Click to show full abstract
Herein, with air-stable chalcogenated stibines (Sb-ER) as organometallic chalcogenating reagents, we developed base-promoted (Z)-hydrochalcogenation of alkynes with DMSO/DMSO-d6 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(sp3)-S(Se) cross-coupling with C(sp3)-X and copper-catalyzed C(sp2)-S(Se) cross-coupling with C(sp2)-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.
Journal Title: Organic letters
Year Published: 2022
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