107116-05-2Relevant articles and documents
In Situ Generation of Silyl Anion Species through Si?B Bond Activation for the Concerted Nucleophilic Aromatic Substitution of Fluoroarenes
Kojima, Kumiko,Nagashima, Yuki,Wang, Chao,Uchiyama, Masanobu
, p. 277 - 280 (2019/04/04)
In situ generated silyl anion species enable the concerted nucleophilic aromatic substitution of fluoroarenes. Model DFT calculations indicated that addition of a base to a silylborane would thermodynamically form a silyl borate complex and then kinetically release a silyl anion species through Si?B bond cleavage, and that the in situ generated silyl anion equivalent would further react with a fluoroarene through a concerted nucleophilic aromatic substitution pathway with an activation barrier of ca. 20 kcal/mol to afford the silylated product with a large energy gain. Experiments confirmed that the defluorosilylation reaction took place smoothly at room temperature simply upon mixing fluoroarenes with commercially available silylborane and NaOtBu. Radical scavenger and radical clock reaction experiments provide further evidence for the in situ generation of the silyl anion.
Palladium-Catalyzed Cross-Coupling of Monochlorosilanes and Grignard Reagents
Vulovic, Bojan,Cinderella, Andrew P.,Watson, Donald A.
, p. 8113 - 8117 (2017/12/08)
Using a palladium catalyst supported by DrewPhos, the alkylation of monochlorosilanes with primary and secondary alkylmagnesium halides is now possible. Arylation with sterically demanding aromatic magnesium halides is also enabled. This transformation ov
Copper-catalyzed arylation of chlorosilanes with grignard reagents
Morita, Eiji,Murakami, Kei,Iwasaki, Masayuki,Hirano, Koji,Yorimitsu, Hideki,Oshima, Koichiro
experimental part, p. 1012 - 1014 (2011/02/26)
Nucleophilic substitution reactions of chlorosilanes with aryl Grignard reagents take place efficiently in the presence of copper(I) iodide to afford tetraorganosilanes.
