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Copper(I)-Catalyzed Regio- and Stereoselective Silaboration of Terminal Allenes.
ACS Org Inorg Au
April 2023
Division of Applied Chemistry, Graduate School of Engineering, Hokkaido University, Sapporo, Hokkaido 060-8628, Japan.
Organic compounds bearing both silyl and boryl groups are important building blocks in organic synthesis because of the adequate reactivity of the silyl and boryl groups and high stereospecificity in their derivatization reactions. The difference in reactivity between the silyl and boryl groups enables stepwise derivatization of these groups to afford complex molecules. Here, we report the copper(I)-catalyzed silaboration of terminal allenes to produce multisubstituted allylic boronates embedded with an alkenyl silane structure.
View Article and Find Full Text PDFBase-Mediated Borylsilylation/Silylation of Ammonium Salts with Silylborane.
Org Lett
August 2021
School of Pharmaceutical Science (Shenzhen), Sun Yat-sen University, Guangzhou 510275, China.
This work describes a base-mediated borylsilylation of benzylic ammonium salts to synthesize geminal silylboronates bearing benzylic proton under mild reaction conditions. Deaminative silylation of aryl ammonium salts was also achieved in the presence of LiOBu. This strategy which is featured with high efficiency, mild reaction conditions, and good functional group tolerance provides efficient routes for late-stage functionalization of amines.
View Article and Find Full Text PDFSynthesis of Functionalized Organoboron/Silicon Compounds by Copper-Catalyzed Coupling of Alkylsilyl Peroxides and Diboron/Silylborane Reagents.
Org Lett
April 2019
Department of Chemistry, Graduate School of Science , Kyoto University, Sakyo, Kyoto 606-8502 , Japan.
The facile synthesis of functionalized organoboron/silicon compounds by copper-catalyzed coupling of alkylsilyl peroxides and diboron/silylborane reagents is reported. The reactions proceed smoothly under mild, neutral conditions in short reaction times to generate organoboron/silicon compounds bearing a ketone moiety, which are useful synthetic intermediates that are otherwise difficult to access. The results of mechanistic investigations suggest the radical-mediated formation of carbon-boron and carbon-silicon bonds via β-scission of alkoxy radicals.
View Article and Find Full Text PDFDirect Introduction of a Dimesitylboryl Group Using Base-Mediated Substitution of Aryl Halides with Silyldimesitylborane.
Chemistry
December 2016
Division of Applied Chemistry and Frontier Chemistry Center, Graduate School of Engineering, Hokkaido University, Sapporo, 060-8628, Japan.
The first dimesitylboryl substitution of aryl halides with a silylborane bearing a dimesitylboryl group in the presence of alkali-metal alkoxides is described. The reactions of aryl bromides or iodides with Ph MeSi-BMes and Na(OtBu) afforded the desired aryl dimesitylboranes in good to high yields and with high borylation/silylation ratios. Selective reaction of the sterically less-hindered C-Br bond of dibromoarenes provided monoborylated products.
View Article and Find Full Text PDFSilylboranes bearing dialkylamino groups on silicon as silylene equivalents: palladium-catalyzed regioselective synthesis of 2,4-disubstituted siloles.
J Am Chem Soc
February 2008
Department of Synthetic Chemistry and Biological Chemistry, Graduate School of Engineering, Kyoto University, Katsura, Kyoto 615-8510, Japan.
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