- Cross-Electrophile C(sp2)?Si Coupling of Vinyl Chlorosilanes
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The cross-electrophile coupling has become a powerful tool for C?C bond formation, but its potential for forging the C?Si bond remains unexplored. Here we report a cross-electrophile Csp2-Si coupling reaction of vinyl/aryl electrophiles with vinyl chlorosilanes. This new protocol offers an approach for facile and precise synthesis of organosilanes with high molecular diversity and complexity from readily available materials. The reaction proceeds under mild and non-basic conditions, demonstrating a high step economy, broad substrate scope, wide functionality tolerance, and easy scalability. The synthetic utility of the method is shown by its efficient accessing of silicon bioisosteres, the design of new BCB-monomers, and studies on the Hiyama cross-coupling of vinylsilane products.
- Duan, Jicheng,Kang, Shaolin,Liu, Xue-Yuan,Qi, Liangliang,Shu, Xing-Zhong,Wang, Ke,Xu, Guang-Li
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supporting information
p. 23083 - 23088
(2020/12/09)
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- Thieme Chemistry Journals Awardees - Where Are They Now? Titanium-Catalyzed Hydroaminoalkylation of Vinylsilanes and a One-Pot Procedure for the Synthesis of 1,4-Benzoazasilines
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Vinylsilanes undergo intermolecular alkene hydroaminoalkylation with secondary amines in the presence of a titanium mono(aminopyridinato) catalyst to give the branched hydroaminoalkylation products with high regioselectivity. Corresponding reactions of a suitable (2-bromophenyl)vinylsilane combined with a subsequent intramolecular Buchwald-Hartwig amination result in the development of an elegant one-pot procedure for the synthesis of 1,4-benzoazasilines.
- Lühning, Lars H.,Rosien, Michael,Doye, Sven
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supporting information
p. 2489 - 2494
(2017/11/04)
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- Sequential Synthesis of Organosilicon-Linked 2-Methoxypyridines by Non-Cryogenic ortho-Metallation Using the nBu2TMPMg·Li Reagent and Hydrosilylation
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The non-cryogenic synthesis of 5/6- and/or 3-silyl-functionalised 2-methoxypyridines by a 5-Br/Mg exchange process using nBu2iPrMg Li and LiCl and involving C-3 metallation using a novel nBu2TMPMg Li reagent is described. Furthermore, the usefulness of nBu2TMPMg Li in the functionalisation of 2-methoxypyridine at the 3-position with a wide range of electrophiles was successfully tested. The above achievements have allowed the construction of organosilicon-linked 2-methoxypyridines composed of two, three and four rings by the hydrosilylation of 5- and/or 3-SiH(or alkenyl) derivatives using the hitherto rarely applied [Pt(cod)Me2] catalyst. Additionally, the synthesis of a one-chain oligomer consisting of eight 2-methoxypyridines obtained by the hydrosilylation/polymerisation approach, followed by protodesilylation of the SiHMe2 group was also achieved by manipulating the amount of catalyst in the reactions.
- Struk, ?ukasz,Sos?nicki, Jacek G.,Idzik, Tomasz J.,Maciejewska, Gabriela
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supporting information
p. 1292 - 1304
(2016/03/19)
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