Categories: C-Si Bond Formation > Silanes
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.
Related
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.