122016-19-7Relevant academic research and scientific papers
A Drastic Effect of TEMPO in Zinc-Catalyzed Stannylation of Terminal Alkynes with Hydrostannanes via Dehydrogenation and Oxidative Dehydrogenation
Kai, Yuichi,Oku, Shinya,Sakurai, Kyoko,Tani, Tomohiro,Tsuchimoto, Teruhisa
supporting information, (2019/08/21)
With a system consisting of a catalytic zinc Lewis acid, pyridine, and TEMPO in a nitrile medium, terminal alkynes coupled with HSnBu3, providing alkynylstannanes with structural diversity. The resulting alkynylstannane, without being isolated, could be directly used for Pd- and Cu-catalyzed transformations to deliver internal alkynes and more intricate tin-atom-containing molecules. Mechanistic studies indicated that TEMPOSnBu3 formed in situ from TEMPO and HSnBu3 works to stannylate the terminal alkyne in collaboration with the zinc catalyst, and that both of dehydrogenation and oxidative dehydrogenation processes are uniquely involved in a single reaction. (Figure presented.).
Catalytic Dehydrogenative Stannylation of C(sp)-H Bonds Involving Cooperative Sn-H Bond Activation of Hydrostannanes
Forster, Francis,Rendón López, Victoria M.,Oestreich, Martin
supporting information, p. 1259 - 1262 (2018/02/09)
The catalytic generation of a stannylium-ion-like tin electrophile by heterolytic cleavage of the Sn-H bond in hydrostannanes at the Ru-S bond of Ohki-Tatsumi complexes is reported. Reacting these activated hydrostannanes with terminal acetylenes does not lead to hydrostannylation of the C-C triple bond but to dehydrogenative stannylation of the alkyne terminus. The scope of this rare direct C(sp)-H bond stannylation with hydrostannanes is broad, and a mechanism involving a β-tin-stabilized vinyl cation likely having a bridged structure is presented.
Direct synthesis of alkynylstannanes: ZnBr2 catalyst for the reaction of tributyltin methoxide and terminal alkynes
Kiyokawa, Kensuke,Tachikake, Nodoka,Yasuda, Makoto,Baba, Akio
, p. 10393 - 10396 (2011/12/04)
Metal hopping: Various alkynylstannanes were synthesized by the direct reaction of Bu3SnOMe with terminal alkynes at room temperature in the presence of a ZnBr2 catalyst. Rather than acting as a Lewis acid, ZnBr2 was transmetalated with Bu3SnOMe to give Zn(OMe)2, which is key to the catalytic reaction. Copyright
