770-09-2Relevant articles and documents
Nickel-Mediated Enantiospecific Silylation via Benzylic C-OMe Bond Cleavage
Balakrishnan, Venkadesh,Murugesan, Vetrivelan,Chindan, Bincy,Rasappan, Ramesh
supporting information, p. 1333 - 1338 (2021/02/20)
Benzylic stereocenters are found in bioactive and drug molecules, as enantiopure benzylic alcohols have been used to build such a stereogenic center, but are limited to the construction of a C-C bond. Silylation of alkyl alcohols has the potential to build bioactive molecules and building blocks; however, the development of such a process is challenging and unknown. Herein, we describe an unprecedented AgF-assisted nickel catalysis in the enantiospecific silylation of benzylic ethers.
Fluoroalkylselenolation of Alkyl Silanes/Trifluoroborates under Metal-Free Visible-Light Photoredox Catalysis
Ghiazza, Clément,Khrouz, Lhoussain,Billard, Thierry,Monnereau, Cyrille,Tlili, Anis
supporting information, p. 1559 - 1566 (2019/11/03)
Herein a metal-free fluoroalkylselenolation of alkylsilanes as well as potassium alkyltrifluoroborates under visible light photocatalysis is disclosed. The developed methodologies are performed under mild conditions, room temperature in the presence of an organic photocatalyst and blue LED irradiation. Mechanistic investigations including luminescence and EPR spectroscopy allow us to shed light on both mechanisms.
Enantioselective Synthesis of Chiral 3-Substituted-3-silylpropionic Esters via Rhodium/Bisphosphine-Thiourea-Catalyzed Asymmetric Hydrogenation
Zhang, Zongpeng,Han, Zhengyu,Gu, Guoxian,Dong, Xiu-Qin,Zhang, Xumu
supporting information, p. 2585 - 2589 (2017/08/16)
We have successfully developed the asymmetric hydrogenation of β-silyl-α,β-unsaturated esters to prepare chiral 3-substituted-3-silylpropionic ester products catalyzed by rhodium/bisphosphine-thiourea (ZhaoPhos) with excellent results (up to 97% yield, >99% ee, 1500 TON). Moreover, our hydrogenation products can be efficiently converted to other important organic molecules, such as chiral ethyl (R)-3-hydroxy-3-phenylpropanoate or (R)-3-[dimethyl(phenyl)silyl]-3-phenylpropanoic acid. (Figure presented.).