Base-Promoted Reactions of Organostibines with Alkynes and Organic Halides to Give Chalcogenated (<i>Z</i>)-Olefins and Ethers
Liyuan Le, Shuangshuang Li, Dejiang Zhang, Shuang‐Feng Yin, Nobuaki Kambe, Renhua Qiu
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.