65549-78-2Relevant academic research and scientific papers
Synthesis of Benzosiloles by Intramolecular anti-Hydroarylation via ortho-C-H Activation of Aryloxyethynyl Silanes
Minami, Yasunori,Noguchi, Yuta,Hiyama, Tamejiro
supporting information, p. 14013 - 14016 (2017/10/17)
Straightforward synthesis of benzosiloles was achieved by the invention of Pd/acid-catalyzed intramolecular anti-hydroarylation of aryloxyethynyl(aryl)silanes via ortho-C-H bond activation. The aryloxy group bound to the ethynyl carbon is the key factor for this transformation.
Mechanistic study on the base-promoted reaction of allylphenylsilanes to alkenylsilanols
Imazeki, Shigeaki,Sugawara, Hiroo,Sano, Atsunori,Akiyama, Takahiko
experimental part, p. 623 - 629 (2009/04/11)
On treatment of allylphenylsilanes with t-BuOK and 18-crown-6 in DMSO, isomerization of the olefinic double bond and subsequent substitution of the phenyl group with a hydroxy group took place smoothly to afford alkenylsilanol derivatives in good yields. The reaction mechanism was investigated using 18O-labeled sulfoxide. We found that a (methylsulfinyl)methyl anion generated from DMSO participated in this reaction.
Modular approach to silicon-bridged biaryls: Palladium-catalyzed intramolecular coupling of 2-(arylsilyl)aryl triflates
Shimizu, Masaki,Mochida, Kenji,Hiyama, Tamejiro
supporting information; body text, p. 9760 - 9764 (2009/05/30)
(Chemical Equation Presented) Bridge of Si: Intramolecular direct arylation of 2-(arylsilyl)aryl triflates is catalyzed smoothly by Pd(OAc) 2/PCy3 in the presence of Et2NH in dimethylacetamide (DMA), giving rise to the corresponding silicon-bridged biaryls in good to excellent yields. The new approach has led to the synthesis of a silicon-bridged 2-phenylindole (see scheme) that exhibits blue photoluminescence in the solid state with extremely high quantum yields.
Intramolecular [3+2]-hetero-annulation of allylsilanes with 1,3-cyclohexanediones and its application in the synthesis of hexacyclic hopane triterpenes
Schinzer,Muller,Fischer,Priess
, p. 1265 - 1268 (2007/10/03)
In this letter we describe the intramolecular [3+2]-hetero-annulation of allylsilanes with 1,3-cyclohexanediones followed by sila-Wagner-Meerwein shift. The new synthesis of the cyclization precursors offers the advantage to vary the silyl terminator at t
Preparation of 2,5-anhydrohexitols (part I). Silicon-directed stereocontrolled cyclization
Van Delft, Floris L.,Valentijn, A. Rob P.M.,Van Der Marel, Gijs A.,Van Boom, Jacques H.
, p. 165 - 190 (2007/10/03)
Stereoselective chain-extension of carbohydrate aldehydes with the hydroxymethylating reagent (dimethylphenylsilyl)methylmagnesium chloride (1) followed by acid-mediated cyclization gives access to 2,5-anhydro-hexitols. The stereoselectivity of the ring closure depends on the nature of the acid, i.e., treatment with excess BF3·Et2O or catalytic H2SO4 leads to tetrahydrofurans with 2,3-cis or 2,3-trans configuration, respectively. Concomitant elimination is effectively suppressed in case of cyclisation of the more sterically hindered isopropyl substituted silanes.
Tandem [4 + 2]/[3 + 2] cycloadditions of nitroalkenes. 13. The synthesis of (-)-detoxinine
Denmark, Scott E.,Hurd, Alexander R.,Sacha, Hubert J.
, p. 1668 - 1674 (2007/10/03)
(-)-Detoxinine, an unusual, highly-functionalized amino acid, is the core residue of many components that comprise the detoxin complex. The synthesis of (-)-detoxinine was accomplished in 10 steps and 13.4% overall yield from commercially available dichlorodiisopropylsilane. The key step is an asymmetric tandem inter [4 + 2]/intra [3 + 2] cycloaddition between silyoxynitroalkene 17 and chiral vinyl ether (-)-24, illustrating the application of a temporary silicon tether in the tandem nitroalkene cycloaddition process.
AN ALTERNATIVE ROUTE TO PERALKYLCYCLOPOLYSILANES: THE REACTION OF 1,2-DICHLOROTETRAALKYLDISILANES WITH LITHIUM
Watanabe, Hamao,Inose, Jun,Fukushima, Koji,Kougo, Yuichi,Nagai, Yoichiro
, p. 1711 - 1714 (2007/10/02)
The reaction of 1,2-dichlorotetraalkyldisilanes, Cl(R1R2Si)2Cl (R1=R2=iPr; R1, R2=iPr, Me; R1, R2=Me3SiCH2, Me; R1, R2=tBuCH2, Me; R1, R2=tBu, Me), with an excess amount of lithium in tetrahydrofuran gave the corresponding peralkylcyclopolysilanes, n (n=4-5), under mild conditions.
