芳烃碳-硅键的构建

硅基直接和芳烃相连接的碳硅键的构建在有机硅行业中具有重要作用，转帖一点相关资料！
来源：
http://www.organic-chemistry.org/synthesis/C1Si/index.shtm
1、烃基芳基硅烷

A zinc-catalyzed nucleophilic substitution reaction of chlorosilanes with organomagnesium reagents affords a broad range of functionalized tetraorganosilanes under mild reaction conditions. The reaction can be performed on large scale.
K. Murakami, H. Yorimitsu, K. Oshima, J. Org. Chem., 2009, 74, 1415-1417.

Various siletanes have been used as substrates for the oxidation of carbon-silicon bonds upon exposure to aqueous fluoride and peroxide. These tetraalkylsilanes offer a combination of stability and reactivity with many practical benefits, including compatibility with silicon protecting groups and electron-rich aromatic rings.
J. D. Sunderhaus, H. Lam, G. B. Dudley, Org. Lett., 2003, 8, 4571-4573.

Rapid, efficient methods enable the preparation of phenols from the oxidation of arylhydrosilanes. Electron-rich aromatics benefit from silane activation via oxidation to the methoxysilane using homogeneous or heterogeneous transition metal catalysis. A combination of these two oxidations into a streamlined flow procedure involves minimal processing of reaction intermediates.
E. J. Rayment, N. Summerhill, E. A. Anderson, J. Org. Chem., 2012, 77, 7052-7060.

A new palladium-catalyzed silylation of aryl chlorides affords desired product in good yield, is tolerant of various functional groups, and provides access to a wide variety of aryltrimethylsilanes from commercially available aryl chlorides. Additionally, a one-pot procedure that converts aryl chlorides into aryl iodides has been developed.
E. McNeill, T. E. Barder, S. L. Buchwald, Org. Lett., 2007, 9, 3785-3788.

A Ni/Cu-catalyzed silylation of unactivated C-O electrophiles derived from phenols or benzyl alcohols offers a wide scope and mild conditions and provides a direct access to synthetically versatile silylated compounds.
C. Zarate, R. Martin, J. Am. Chem. Soc., 2014, 136, 2236-2239.

By treatment with s-BuLi/TMEDA at -78°C, unprotected 2-methoxybenzoic acid is deprotonated exclusively in the position ortho to the carboxylate. A reversal of regioselectivity is observed when the acid is treated with n-BuLi/t-BuOK.
T.-H. Nguyen, A.-S. Castanet, J. Mortier, Org. Lett., 2006, 8, 765-768.

Related

Treatment of substituted arylbromides with tert-butyllithium in diethyl ether at -78˚C, followed by the addition to dichlorodiethoxysilane, leads to the quantitative formation of diaryldiethoxysilanes. Diaryldiethoxysilanes can be reduced to the corresponding diarylsilanes by stirring with lithium aluminum hydride in diethyl ether. This method avoids the handling of gaseous and explosive dichlorosilane.
P. Gigier, W. A. Herrmann, F. E. Kühn, Synthesis, 2010, 1431-1432.

2、烷氧基芳基硅烷

General reaction conditions for the synthesis of aryl(trialkoxy)silanes from aryl Grignard and lithium reagents and tetraalkyl orthosilicates (Si(OR)4) have been developed. Ortho-, meta-, and para-substituted bromoarenes underwent efficient metalation and silylation at low temperature to provide aryl siloxanes.
A. S. Manoso, C. Ahn, A. Soheili, C. J. Handy, R. Correia, W. Seganish, P. DeShong, J. Org. Chem., 2004, 69, 8305-8314.

A. S. Manoso, C. Ahn, A. Soheili, C. J. Handy, R. Correia, W. Seganish, P. DeShong, J. Org. Chem., 2004, 69, 8305-8314.

High yields were achieved by using [Rh(cod)(MeCN)2]BF4 as catalyst in a specific silylation of aryl iodides and bromides with triethoxysilane in the presence of NEt3. This new reaction tolerates different functional groups and therefore often eliminates the need to use protective groups (compared to previous methods via Grignard reagents).
M. Murata, M. Ishikura, M. Nagata, S. Watanabe, Y. Masuda, Org. Lett., 2002, 4, 1843-1845.

The silylation of various aryl iodides with 1,1,1,3,5,5,5-heptamethyltrisiloxane was achieved using transition-metal catalysts, such as Pd(0), Pt(0), and Rh(I), which offer a dramatically different substrate scope.
M. Murata, K. Ota, H. Yamasaki, S. Watanabe, Y. Masuda, Synlett, 2007, 1387-1390.

An efficient rhodium-catalyzed method allows the preparation of aryltriethoxysilanes from arenediazonium tosylate salts. A new method for hydrodediazoniation has also been explored.
Z. Y. Tang, Y. Zhang, T. Wang, W. Wang, Synlett, 2010, 804-808.

Treatment of substituted arylbromides with tert-butyllithium in diethyl ether at -78˚C, followed by the addition to dichlorodiethoxysilane, leads to the quantitative formation of diaryldiethoxysilanes. Diaryldiethoxysilanes can be reduced to the corresponding diarylsilanes by stirring with lithium aluminum hydride in diethyl ether. This method avoids the handling of gaseous and explosive dichlorosilane.
P. Gigier, W. A. Herrmann, F. E. Kühn, Synthesis, 2010, 1431-1432.

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