18666-43-8Relevant academic research and scientific papers
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.
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.
Br?nsted acid-promoted formation of stabilized silylium ions for catalytic friedel-crafts C-H silylation
Chen, Qing-An,Klare, Hendrik F. T.,Oestreich, Martin
supporting information, p. 7868 - 7871 (2016/07/07)
A counterintuitive approach to electrophilic aromatic substitution with silicon electrophiles is disclosed. A strong Br?nsted acid that would usually promote the reverse reaction, i.e., protodesilylation, was found to initiate the C-H silylation of electron-rich (hetero)arenes with hydrosilanes. Protonation of the hydrosilane followed by liberation of dihydrogen is key to success, fulfilling two purposes: to generate the stabilized silylium ion and to remove the proton released from the Wheland intermediate.
Integrated palladium-catalyzed arylation of heavier groupa 14 hydrides
Lesbani, Aldes,Kondo, Hitoshi,Yabusaki, Yusuke,Nakai, Misaki,Yamanoi, Yoshinori,Nishihara, Hiroshi
supporting information; experimental part, p. 13519 - 13527 (2011/02/24)
A convenient procedure has been developed for the preparation of Groupa 14 compounds by integrated palladium-catalyzed cross-coupling of aromatic iodides with the corresponding Groupa 14 hydrides in the presence of a base. The reaction conditions can be applied to the cross-coupling of tertiary, secondary, and primary Groupa 14 compounds. In most cases, the desired arylated products were obtained in synthetically useful yields. Even in the case of aryl iodides containing OH, NH2, CN, or CO2R groups, the reactions proceeded with good to high yields with tolerance of these reactive functional groups. A possible application of this method is the unique synthesis of a fungicidal diarylmethyl(1H-1,2,4-triazol-1-ylmethyl)silane derivative. A convenient procedure has been developed for the preparation of Groupa 14 compounds by integrated palladium-catalyzed cross-coupling of aromatic iodides with the corresponding Groupa 14 hydrides in the presence of a base (see picture). Application of this method in the synthesis of a fungicidal diarylmethyl(1H-1,2,4-triazol-1-yl-methyl)silane derivative is demonstrated. Copyright
