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Synthesis of benzylsilanes

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Gold nanoparticles supported on ZrO2 efficiently generate alkyl radicals via homolysis of unactivated C(sp3)-O bonds. A subsequent C(sp3)-Si bond formation provides diverse organosilicon compounds. A wide array of esters and ethers participated in the heterogeneous gold-catalyzed silylation by disilanes to give diverse alkyl-, allyl-, benzyl-, and allenyl silanes in high yields.
H. Miura, M. Doi, Y. Yasui, Y. Masaki, H. Nishio, T. Shishido, J. Am. Chem. Soc., 2023, 145, 4613-4625.


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.


A cobalt-catalyzed enantioselective hydrosilylation of terminal alkenes enables an efficient synthesis of valuable chiral dihydrosilanes. This protocol is operationally simple and atom-economic using relatively simple and readily available starting materials.
B. Cheng, P. Lu, H. Zhang, X. Cheng, Z. Lu, J. Am. Chem. Soc., 2017, 139, 9439-9442.


Phosphonium salts catalyze a coupling of both activated and nonactivated alkyl halides with both trichlorosilane and methyldichlorosilane. A wide variety of silyl-functionalized compounds may be prepared easily and in good yields.
Y. S. Cho, S.-H. Kang, J. S. Han, B. R. Yoo, I. N. Jung, J. Am. Chem. Soc., 2001, 123, 5584-5585.


A novel catalytic system for the asymmetric hydrosilylation of aromatic alkenes is described, which leads to silanes in high yields and with excellent enantioselectivity. The reaction works efficiently for a variety of substituted aromatic alkenes, giving access after Tamao oxidation to almost optically pure benzylic alcohols in high yields.
J. F. Jensen, B. Y. Svendsen, T. V. la Cour, H. L. Pedersen, M. Johannsen, J. Am. Chem. Soc., 2002, 124, 4558-4559.


A titanocene complex catalyzes a regioselective carbosilylation of terminal alkenes and 2,3-disubstituted 1,3-butadienes with alkyl halides and chlorotrialkylsilanes efficiently at 0°C in THF in the presence of Grignard reagents. Terminal alkenes afford addition products in good yields, whereas in reaction with dienes, alkyl and silyl units are introduced at the 1- and 4-positions to provide allylsilanes.
S. Nii, J. Terao, N. Kambe, J. Org. Chem., 2000, 65, 5291-5297.


Electroreduction of readily available chlorosilanes enables a new strategy for silyl radical generation via energetically uphill reductive cleavage of strong Si-Cl bonds at highly biased potentials. This convenient and transition-metal-free strategy proved to be general in various alkene silylation reactions including disilylation, hydrosilylation, and allylic silylation.
L. Lu, J. C. Siu, Y. Lai, S. Lin, J. Am. Chem. Soc., 2020, 142, 20979-20986.


A chiral spiro-bisoxazoline ligand has proven to be an optimal ligand for an asymmetric iron-catalyzed enantioselective Si-H bond insertion reaction of α-diazoesters to provide chiral α-silyl esters in good yields with high enantioselectivities. The reaction proceeds via a concerted quintet transition state.
H. Gu, Z. Han, H. Xie, X. Lin, Org. Lett., 2018, 20, 6544-6549.


An efficient carbene insertion reaction of α-diazoesters into Si-H bond provides a wide range of α-silylesters in high yields using a simple iron(II) salt as catalyst.
H. Keipour, T. Ollevier, Org. Lett., 2017, 19, 5736-5739.


Sm/SmI2 mediates the generation of α-aminocarbene intermediates from amide precursors for Pd-catalyzed Si-H insertion reactions to provide α-aminosilanes. This deoxygenative cross-coupling of amides and silanes offers simplicity and versatility.
J. Jiao, W. Yang, X. Wang, J. Org. Chem., 2023, 88, 594-601.

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The Rh-catalyzed cross-coupling between ArZnI and TMSCH2I gave various functionalized benzylsilanes in good yields. A mechanism is proposed.
H. Takahashi, K. M. Hossain, Y. Nishihara, T. Shibata, K. Takagi, J. Org. Chem., 2006, 71, 671-675.