204651-34-3Relevant 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
, (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.).
Palladium-iminophosphine-catalyzed alkynylstannylation of alkynes
Yoshida, Hiroto,Shirakawa, Eiji,Kurahashi, Takuya,Nakao, Yoshiaki,Hiyama, Tamejiro
, p. 5671 - 5678 (2008/10/08)
A palladium complex coordinated by an iminophosphine ligand was found to catalyze the addition of alkynylstannanes to a carbon - carbon triple bond of various alkynes in moderate to good yields with exclusive syn selectivity. The alkynyl group in the stannanes was attached mainly to the internal carbon of terminal alkynes, except for 1-alkyn-3-ones and alkynoates, where the alkynyl group was connected to the terminal carbon. Steric bulk of the ligand markedly influenced on the regioselectivity and reaction rate: an iminophosphine with a bulkier imino moiety accelerated the alkynylstannylation with higher regioselectivity. On the basis of these observations, the mechanism of the present reaction is discussed.
The palladium-iminophosphine catalyst for the reactions of organostannanes
Shirakawa, Eiji,Hiyama, Tamejiro
, p. 169 - 178 (2007/10/03)
A palladium complex coordinated by an iminophosphine ligand was found to be a remarkably active catalyst for the coupling of organostannanes with aryl halides. The mechanistic studies show that the reaction of an alkynylstannane proceeds through an unprecedented catalytic cycle which involves an oxidative addition of the organostannane to the Pd(0)-iminophosphine complex. The catalyst was demonstrated to be also useful for the carbostannylation of alkynes and the homocoupling reaction of organostannanes.
