79328-17-9Relevant academic research and scientific papers
Palladium-Catalyzed Benzylic Silylation of Diarylmethyl Carbonates with Silylboranes under Base-Free Conditions
Asai, Kento,Hirano, Koji,Miura, Masahiro
supporting information, (2022/02/19)
A palladium-catalyzed benzylic silylation of diarylmethyl carbonates with silylboranes has been developed. The reaction proceeds smoothly even under external base-free conditions, and the corresponding benzylic silanes are formed in good to high yields. The obtained benzyl silane derivatives can work as the benzylic nucleophiles by the action of a suitable fluoride source and react with some carbon electrophiles to deliver the corresponding benzylic C?C cross-coupled products. Additionally, while still preliminary, the allylic silylation of the isoelectronic allylic carbonates is also achieved.
Synthesis of Allylsilanes via Nickel-Catalyzed Cross-Coupling of Silicon Nucleophiles with Allyl Alcohols
Yang, Bo,Wang, Zhong-Xia
, p. 7965 - 7969 (2019/10/19)
NiCl2(PMe3)2-catalyzed reaction of allyl alcohols with silylzinc reagents, including PhMe2SiZnCl, Ph2MeSiZnCl, and Ph3SiZnCl, was performed, achieving allylsilanes in high yields. Aryl- and heteroaryl-substituted allyl alcohols, (E)-3-arylprop-2-en-1-ols, 1-aryl-prop-2-en-1-ols, and (E)-1-phenylpent-1-en-3-ol can be employed in the transformation. A range of functional groups as well as heteroaryl groups were tolerated. Reaction exhibited high regioselectivity and E/Z-selectivity when 1- or 3-aryl-substituted allyl alcohols were used as the substrates. Reaction of chiral allyl alcohol, (S,E)-1-phenylpent-1-en-3-ol, yielded a configuration-inversion product (R,E)-dimethyl(phenyl)(1-phenylpent-1-en-3-yl)silane.
Cu(I)-NHC-Catalyzed Silylation of Allenes: Diastereoselective Three-Component Coupling with Aldehydes
Rae, James,Hu, Ya Chu,Procter, David J.
supporting information, p. 13143 - 13145 (2016/02/19)
Copper-catalyzed silylation of aryl allenes using a silylborane reagent affords vinyl silane building blocks with high efficiency. The use of a seven-membered NHC ligand proved crucial for high regioselectivity. The catalytically generated allylcoppper intermediates were intercepted by aldehydes in a diastereoselective three-component coupling to furnish homoallylic alcohols. Seven′s up! The use of a seven-membered N-heterocyclic carbene (NHC) ligand proved crucial in exerting high regiocontrol during the development of the first copper-catalyzed silylation of allenes using a commercial silylborane reagent. The process affords privileged vinyl silane building blocks with high efficiency. Allylcopper intermediates can be intercepted by aldehydes in a highly diastereoselective three-component coupling to furnish homoallylic alcohols.
Electrochemical Synthesis of Organosilicon Compounds
Yoshida, Jun-ichi,Muraki, Katsuhiko,Funahashi, Hirokatsu,Kawabata, Nariyoshi
, p. 3996 - 4000 (2007/10/02)
Electrochemical reduction of allyl, aryl, and vinyl halides in the presence of a silylating agent (Me3SiCl, HMe2SiCl, and PhMe2SiCl) in a solution of tetraethylammonium tosylate in dimethylformamide (DMF) gave the corresponding organosilicon compounds.The regioselectivity of the reaction of allylic halides depends on the nature of the silylating agent.Trimethylsilyl and dimethylphenylsilyl groups were introduced to the less substituted end of the allyl group, whereas the dimethylsilyl group was introduced to both ends of the allyl group.High chemoselectivity of the present approach was demonstrated by selectivity monosilylations of p-bromoiodobenzene and p-bromocinnamyl chloride to obtain (p-bromophenyl)trimethylsilane and (p-bromocinnamyl)trimethylsilane, respectively.A mechanism involving a carbanion intermediate is suggested.
