18840-19-2Relevant academic research and scientific papers
Ruthenium-Catalyzed Isomerization of ortho-Silylanilines to Their para Isomers
Ishiga, Wataru,Ohta, Masaya,Kodama, Takuya,Tobisu, Mamoru
supporting information, p. 6714 - 6718 (2021/09/02)
The catalytic ortho to para transposition of a silyl group in aniline derivatives is described. [RuCl2(p-cymene)]2/BINAP in conjunction with a Cu(OAc)2 additive serves as a potent catalytic system. This method is also applicable to the isomerization of 2-silylpyrrole derivatives to the corresponding 3-silyl isomers.
Boron-Catalyzed Aromatic C-H Bond Silylation with Hydrosilanes
Ma, Yuanhong,Wang, Baoli,Zhang, Liang,Hou, Zhaomin
supporting information, p. 3663 - 3666 (2016/04/09)
Metal-free catalytic C-H silylation of a series of aromatic compounds such as N,N-disubstituted anilines with various hydrosilanes has been achieved for the first time using commercially available B(C6F5)3 as a catalyst. This protocol features simple and neutral reaction conditions, high regioselectivity, wide substrate scope (up to 40 examples), Si-Cl bond compatibility, and no requirement for a hydrogen acceptor.
Friedel-Crafts-Type Intermolecular C-H Silylation of Electron-Rich Arenes Initiated by Base-Metal Salts
Yin, Qin,Klare, Hendrik F. T.,Oestreich, Martin
supporting information, p. 3204 - 3207 (2016/03/12)
An electrophilic aromatic substitution (SEAr) with a catalytically generated silicon electrophile is reported. Essentially any commercially available base-metal salt acts as an initiator/catalyst when activated with NaBArF4. The thus-generated Lewis acid then promotes the SEAr of electron-rich arenes with hydrosilanes but not halosilanes. This new C-H silylation was optimized for FeCl2 /NaBArF4, affording good yields at catalyst loadings as low as 0.5 mol %. The procedure is exceedingly straightforward and comes close to typical Friedel-Crafts methods, where no added base is needed to absorb the released protons.
Palladium-catalyzed silylations of hydrosilanes with aryl halides using bulky alkyl phosphine
Yamanoi, Yoshinori
, p. 9607 - 9609 (2007/10/03)
A palladium-catalyzed direct trialkylsilyl transfer to aryl halides has been developed. In the presence of Pd(t-Bu3P)2 and K 3PO4, electron-rich para- or meta-substitute aryl iodides were coupled efficiently with triethylsilane, triphenylsilane, and dimethylphenylsilane to afford the corresponding silylated products in moderate to good yields.
